Organization
Scheduled update Special-Appointment Professor
Position
Special-Appointment Professor
External link
HANAYA Tadashi
Degree
-
学術博士 ( 岡山大学 )
Research Interests
-
Synthetic Organic Chemistry
-
Carbohydrate Chemistry
-
Heterocyclic Chemistry
-
合成有機化学
-
糖質化学
-
複素環化学
Research Areas
-
Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry
-
Life Science / Bioorganic chemistry
Education
-
Okayama University 大学院理学研究科 化学専攻
1982.4 - 1984.3
Country： Japan
-
Okayama University 理学部 化学科
1978.4 - 1982.3
Country： Japan
Research History
-
Okayama University 教育推進機構 Professor Professor
2025.4
-
Professor, Okayama University
2022.4
-
Okayama University 教育推進機構 Professor
2022.4 - 2025.3
-
Okayama University Institute for Education and Student Services Professor
2016.4 - 2022.3
-
Okayama University Center for Faculty Development Professor
2014.4 - 2016.3
-
Okayama University The Graduate School of Natural Science and Technology Associate Professor
2005.4 - 2014.3
-
Okayama University 理学部化学科 Associate Professor (as old post name)
2003.4 - 2005.3
-
岡山大学 機器分析センター 助教授
1997.4 - 2003.3
-
Okayama University The Graduate School of Natural Science and Technology Research Assistant
1996.4 - 1997.3
-
Okayama University Faculty of Science Research Assistant
1986.5 - 1996.3
Professional Memberships
-
日本化学会
-
有機合成化学協会
Papers
-
First Total Synthesis of Cyanopterin, a Pterin Glycoside Isolated from a Cyanobacterium Reviewed
T. Hanaya, Y. Maeda, K. Ejiri
Carbohydr. Res. 558 109710 2025
-
Synthesis of biopterin and related pterin glycosides Reviewed
Tadashi Hanaya, Hiroshi Yamamoto
IUBMB Life 65 ( 4 ) 300 - 309 2013.4
-
Synthetic studies on pterin glycosides: the first synthesis of 2 '-O-(alpha-D-glucopyranosyl)biopterin Reviewed
Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto
TETRAHEDRON 65 7989 - 7997 2009
-
Inclusion complexation of 4′,6‑diamidino‑2‑phenylindole (DAPI) with cucurbit[7]uril and cyclodextrins (native β‑, 2,6‑di‑O‑methylated β‑, and γ‑cyclodextrin): characteristic inclusion behavior and fluorescence enhancement Reviewed
Y. Sueishi, S. Hagiwara, N. Inazumi, T. Hanaya
J. Incl. Phenom. Macrocycl. Chem. 99 ( 3-4 ) 209 - 216 2021
-
Comparative study of inclusion complexation of tetraalkylphosphonium and ammonium salts with cucurbit[7]uril Reviewed
Y. Sueishi, S. Hagiwara, Y. Matsumoto, T. Hanaya
J. Incl. Phenom. Macrocycl. Chem. 98 117 - 122 2020
-
Characterization of group‑inclusion complexations of rhodamine derivatives with native and 2,6‑di‑O‑methylated β‑cyclodextrins Reviewed
Y. Sueishi, Y. Matsumoto, Y. Kimata, Y. Osawa, N. Inazumi, T. Hanaya
J. Incl. Phenom. Macrocycl. Chem. 96 ( 3-4 ) 365 - 372 2020
-
Characterization of inclusion complexation of various tetraalkylammonium chlorides with cucurbit[7]uril by external highpressure studies Reviewed
Y. Matsumoto, N. Inazumi, T, Hanaya, Y. Sueishi
J. Incl. Phenom. Macrocycl. Chem. 92 ( 1-2 ) 205 - 210 2018
-
A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin Reviewed
Y. Sueishi, A. Itoh, N. Inazumi, Y. Osawa, T. Hanaya
J. Incl. Phenom. Macrocycl. Chem. 91 ( 1-2 ) 1 - 7 2018
-
Efficient Total Syntheses of Natural Neopterin Glycosides: Neopterin Glucronide and Solfapterin Reviewed
T. Hanaya, K. Iwasaki, K, Saeki, T. Hattori
Heterocycles 95 390 - 409 2017
-
Inclusion complexation abilities of cucurbit[6]uril for various aromatic amines in the presence of alkali metal cations Reviewed
Yusaku Honda, Tadashi Hanaya, Yoshimi Sueishi
J. Incl. Phenom. Macrocycl. Chem. 88 253 - 257 2017
-
Influence of Counter Anions on Inclusion Complexation of p-Sulfonatocalix[6] arene with 1-Butyl-3-methylimidazolium Salts (Ionic Liquids) Reviewed
Yusaku Honda, Shono Fujitani, Sho Tamaki, Naoya Inazumi, Tadashi Hanaya, Yoshimi Sueishi
ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS 230 ( 8 ) 1153 - 1164 2016.8
-
Investigation of inclusion complexation of imidazolium and pyrrolidinium chlorides with water-soluble p-sulfonatocalix[6]arene: characteristic effects of external pressure, temperature, and substituents Reviewed
Yoshimi Sueishi, Yusaku Honda, Shono Fujitani, Naoya Inazumi, Tadashi Hanaya
J. Incl. Phenom. Macrocycl. Chem. 86 255 - 261 2016
-
Characteristically steric effects of substituent on bidirectional inclusion complexation of alpha-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxides with beta-cyclodextrins Reviewed
Keitaro Miyazono, Tadashi Hanaya, Yoshimi Sueishi
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY 83 ( 1-2 ) 193 - 197 2015.10
-
Characteristic effects of substituent and external pressure on group- inclusion complexation with p-sulfonatocalix[8]arene and gamma-cyclodextrin Reviewed
Keitaro Miyazono, Tadashi Hanaya, Yoshimi Sueishi
HIGH PRESSURE RESEARCH 34 ( 3 ) 337 - 344 2014
-
Selective Preparation of 6- and 7-(Polyhydroxypropyl)pterins from Pentos-2-uloses Reviewed
T. Hanaya, K. Ito
Heterocycles 88 1491 - 1499 2014
-
First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae Reviewed
Tadashi Hanaya, Hiroshi Yamamoto
PTERIDINES 24 ( 1 ) 3 - 6 2013.6
-
SYNTHESIS OF 2-ACETAMIDO-2,5-DIDEOXY-5-PHOSPHORYL-D-GLUCOPYRANOSE DERIVATIVES: NEW PHOSPHA-SUGAR ANALOGS OF N-ACETYL-D-GLUCOSAMINE Reviewed
Tadashi Hanaya, Masahiro Kawaguchi, Masakazu Sumi, Kazuo Makino, Keiko Tsukada, Hiroshi Yamamoto
HETEROCYCLES 86 ( 2 ) 1147 - 1165 2012.12
-
SYNTHETIC STUDIES ON NATURAL PTERIN GLYCOSIDES Invited Reviewed
Tadashi Hanaya, Hiroshi Yamamoto
Heterocycles 85 2375 - 2390 2012
-
FIRST SYNTHESIS OF A NATURAL ISOXANTHOPTERIN GLYCOSIDE, ASPEROPTERIN-A Reviewed
Tadashi Hanaya, Kazumasa Ejiri, Hiroshi Yamamoto
HETEROCYCLES 84 801 - 813 2012
-
AN EFFICIENT SYNTHESIS OF ANTIBIOTIC SF-2312 (3-DIHYDROXYPHOSPHORYL-1,5-DIHYDROXY-2-PYRROLIDONE) Reviewed
Tadashi Hanaya, Chika Itoh
Heterocycles 82 1675 - 1683 2011
-
Synthesis of 6-hydroxymethylpterin α- and β-D-glucosides Reviewed
T. Hanaya, H. Baba, K. Ejiri, H. Yamamoto
Heterocycles 80 1013 - 1025 2010
-
First Synthesis of a Natural Neopterin Glycoside: 3’-O-(β-D-Glucopyranosyluronic acid)neopterin Reviewed
T. Hanaya, T. Hattori, D. Takayama, H. Yamamoto
Pteridines 21 79 - 83 2010
-
FIRST SYNTHESIS OF BIOPTERIN alpha-D-GLUCOSIDE Reviewed
Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto
HETEROCYCLES 77 747 - 753 2009
-
First Synthesis of a Representative, Natural Pterin Glycoside: 2 '-O-(alpha-D-Glucopyranosyl) biopterin Reviewed
Tadashi Hanaya, Hiroshi Yamamoto, Wolfgang Pfleiderer
PTERIDINES 20 36 - 41 2009
-
NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified beta-cyclodextrins Reviewed
Yoshimi Sueishi, Naoya Inazumi, Tadashi Hanaya
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY 64 ( 1-2 ) 135 - 141 2009
-
AN EFFICIENT SYNTHETIC ROUTE FOR A VERSATILE CILIAPTERIN DERIVATIVE AND THE FIRST CILIAPTERIN D-MANNOSIDE SYNTHESIS Reviewed
Tadashi Hanaya, Hiroki Baba, Mitsunori Kanemoto, Hiroshi Yamamoto
HETEROCYCLES 76 635 - 644 2008
-
Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin Reviewed
Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto
TETRAHEDRON 64 ( 9 ) 2090 - 2100 2008
-
An Efficient Synthesis of 2 '-O-(beta-D-Ribofuranosyl)biopterin Reviewed
Tadashi Hanaya, Kiyoshi Torigoe, Kazuyuki Soranaka, Hiroshi Fujita, Hiroshi Yamamoto, Wolfgang Pfleiderer
PTERIDINES 19 ( 3 ) 72 - 78 2008
-
First synthesis of tepidopterin [2 '-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-threo-biopterin] Reviewed
Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto
Carbohydr. Res. 342 ( 15 ) 2159 - 2162 2007
-
The first chemical synthesis of 6-thio-D-fructo-pyranose via methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside as a key intermediate Reviewed
Tadashi Hanaya, Nobuaki Sato, Hiroshi Yamamoto
HETEROCYCLES 71 517 - 522 2007
-
An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal Reviewed
Tadashi Hanaya, Yuichi Nakamura, Hiroshi Yamamoto
Heterocycles 74 983 - 989 2007
-
Improved syntheses of D-ribo- and 2-deoxy-D-ribofuranose phospho sugars from methyl beta-D-ribopyranoside Reviewed
Tadashi Hanaya, Yuko Koga, Heizan Kawamoto, Hiroshi Yamamoto
Heterocycles 73 581 - 591 2007
-
A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar Reviewed
Tadashi Hanaya, Hiroyuki Tsukui, Naomi Igi, Ayashi Noguchi, Heizan Kawamoto, Hiroshi Yamamoto
Heterocycles 72 411 - 420 2007
-
Synthesis of 6- and 7-(1,2,3-trihydroxy-1,2-O-isopropylidenepropyl)pteridines and deoxygenation of their 3 '-hydroxy groups Reviewed
Tadashi Hanaya, Daisuke Takayama, Hiroshi Yamamoto
HETEROCYCLES 70 355 - 365 2006
-
Synthesis of functionalized phospholane oxides and phosphorinane oxides from 1,4- and 1,5-di-O-mesyloxy compounds Reviewed
Tadashi Hanaya, Karsten Schurrle, Hiroshi Yamamoto
Heterocycles 69 ( 1 ) 283 - 294 2006
-
Novel preparation of a 2 '-O-acetyl-1 '-O-(4-methoxybenzyl)-L-biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides Reviewed
Tadashi Hanaya, Hiroki Toyota, Hiroshi Yamamoto
SYNLETT 2075 - 2078 2006
-
An efficient synthesis of 2 '-O-(beta-D-glucopyranosyl)- and 2 '-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-biopterins Reviewed
T Hanaya, K Soranaka, K Harada, H Yamaguchi, R Suzuki, Y Endo, H Yamamoto, W Pfleiderer
Heterocycles 67 299 - 310 2006
-
Differential effects of substituent and pressure on induced inclusion complexation of 6-O-alpha-D-glucosyl-beta-cyclodextrin with 4-substituted phenols Reviewed
Yoshimi Sueishi, Naoya Inazumi, Tatsuhiro Ide, Tadashi Hanaya
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY 54 201 - 208 2006
-
Synthesis of phospholane 1-oxide having oxygen functional groups from a 4-bromobutylphoshinate derivative Reviewed
T Hanaya, S Kawase, H Yamamoto
Heterocycles 66 251 - 261 2005.12
-
An efficient synthesis of methyl 1,3-O-isopropylidene-alpha-D-fructofuranoside and 2,3 : 5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose Reviewed
T Hanaya, N Sato, H Yamamoto
Carbohydr. Res. 340 2494 - 2501 2005.11
-
Effects of pressure on inclusion complexation of methylene blue with water-soluble p-sulfonatocalix[n]arenes Reviewed
Y Sueishi, N Inazumi, T Hanaya
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY 18 ( 5 ) 448 - 455 2005.5
-
Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-D-fructopyranose derivatives Reviewed
T Hanaya, K Imai, YV Prikhod'ko, H Yamamoto
CARBOHYDRATE RESEARCH 340 ( 1 ) 31 - 37 2005.1
-
Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (alpha-hydroxyphosphonates) Reviewed
T Hanaya, K Sugiyama, H Kawamoto, H Yamamoto
CARBOHYDRATE RESEARCH 338 ( 16 ) 1641 - 1650 2003.7
-
Synthesis and structure analyses, of 1,2,4-tri-O-acetyl-3,5-di-deoxy-5-C-(isopropyl- and phenyl-phosphinyl)-D-erythro-pentopyranoses Reviewed
T Oshikawa, K Seo, M Yamashita, T Hanaya, Y Hamauzu, H Yamamoto
HETEROCYCLIC COMMUNICATIONS 9 ( 6 ) 559 - 566 2003
-
Synthesis and structural analyses of 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C(isopropylphosphinyl)-D-erythro-pentopyranoses Reviewed
T Oshikawa, K Seo, M Yamashita, T Hanaya, Y Hamauzu, H Yamamoto
Carbohydr. Res. 338 283 - 291 2003
-
Synthesis of Sugar Analogs Having a Phosphorus Atom in the Pyranose Ring (Phospha Sugar) and Stereoselectivity of C-P Bond Introduction Invited Reviewed
T. Hanaya, H. Yamamoto
9 1 - 18 2003
-
A new route for preparation of 5-deoxy-5-(hydroxyphosphinyl)-D-mannopyranose and -L-gulopyranose derivatives Reviewed
T Hanaya, H Yamamoto
HELVETICA CHIMICA ACTA 85 ( 9 ) 2608 - 2618 2002
-
Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose Reviewed
T Hanaya, K Sugiyama, Y Fujii, A Akamatsu, H Yamamoto
Heterocycles 55 1301 - 1309 2001
-
A new route for preparation of 5-deoxy-5-hydroxyphosphinyl-D-gluco- and L-idopyranose derivatives Reviewed
T Hanaya, Y Fujii, S Ikejiri, H Yamamoto
HETEROCYCLES 50 ( 1 ) 323 - 332 1999.1
-
Synthesis of 2-amino-2,5-dideoxy-5-hydroxyphosphinyl-D-mannopyranose derivatives: New phospho-sugar analogues of D-mannosamine Reviewed
T Hanaya, Y Fujii, H Yamamoto
JOURNAL OF CHEMICAL RESEARCH-S ( 12 ) 790 - 791 1998.12
-
Effect of a phosphorus atom upon vicinal H-1-H-1 coupling constants in pyranose derivatives having a C-P bond: Additivity rule for the effect of phosphorus substituents Reviewed
T Hanaya, H Yamamoto
CARBOHYDRATE RESEARCH 306 ( 1-2 ) 157 - 162 1998.1
-
An efficient synthesis of limipterin [2'-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-biopterin] via N-2-(N,N-dimethylamino)-methylene-3-[2-(4-nitrophenyl)ethyl]-L-biopterin Reviewed
H Yamamoto, T Hanaya, K Harada, H Kawamoto, W Pfleiderer
PTERIDINES 7 ( 3 ) 110 - 112 1996.9
-
PTERIDINES .105. SELECTIVE N(3)-AND O(4)-ALKYLATION OF L-BIOPTERIN - A CONVENIENT SYNTHESIS OF 3-METHYL-L-BIOPTERIN AND O(4)-METHYL-L-BIOPTERIN AND THE VERSATILE N(2)-(N,N-DIMETHYLAMINOMETHYLENE)-N(3)-P-NITROPHENETHYL-PROTECTED L-BIOPTERIN Reviewed
T HANAYA, K TORIGOE, K SORANAKA, H YAMAMOTO, QZ YAO, W PFLEIDERER
PTERIDINES 6 ( 1 ) 1 - 7 1995.3
-
FACILE FORMATION OF 2-OXO-1,2-OXAPHOSPHORINANE FROM 1,4-DIHALO-2,3-DIMETHOXYBUTANE - A NEW PREPARATIVE ROUTE TO A 1-PHOSPHONO-PENTOPYRANOSE Reviewed
T HANAYA, A AKAMATSU, S KAWASE, H YAMAMOTO
JOURNAL OF CHEMICAL RESEARCH-S 194 - 195 1995
-
SYNTHESIS OF 6-AMINO-5,6-DIDEOXY-5-HYDROXYPHOSPHINYL-D-GLUCOPYRANOSE Reviewed
T HANAYA, Y FUJII, H YAMAMOTO
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 67 2596 - 2599 1994
-
Synthesis of 1,2,3,4,6-Penta-O-acetyl-5-deoxy-phenylphsophonothioyl-D-glucopyranoses Reviewed
T. Hanaya, A. Akamatsu, T. Isono, H. Yamamoto
J. Chem. Res. (S) 434 - 435 1994
-
NOVEL EFFICIENT SYNTHESIS AND STRUCTURAL-ANALYSIS OF FURANOSE-TYPE PHOSPHONO SUGARS Reviewed
M YAMASHITA, A YABUI, T OSHIKAWA, T HANAYA, H YAMAMOTO
Heterocycles 38 1449 - 1452 1994
-
Novel Stereoselective Preparation and Conformational Analysis of Furanose-Type Phosphono Sugar C-Glycosides Reviewed
A YABUI, M YAMASHITA, T OSHIKAWA, T HANAYA, H YAMAMOTO
CHEMISTRY LETTERS ( 1 ) 93 - 96 1993.1
-
SYNTHESIS OF SUGAR ANALOGS HAVING A PHOSPHORUS ATOM IN THE HEMIACETAL RING (PHOSPHORO SUGAR) Invited Reviewed
T HANAYA, H YAMAMOTO
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 51 377 - 387 1993
-
Synthesis of 6-Deoxy-6-phenylphosphonoyl-D-fructopyranoses : The First Phosphorus-in-the-Ring Analogues of a Ketose Reviewed
T. Hanaya, R. Okamoto, Y. V. Prikhod'ko, M.-A. Armour, A. M. Hogg, H. Yamamoto
J. Chem. Soc. Perkin Trans. 1 1663 - 1671 1993
-
Stereoselectivity in the preparation of 5,6-dideoxy-5- dimethoxyphosphinyl-D- and -L-hexofuranoses, and an efficient synthesis of 5,6-dideoxy-5-hydroxyphosphinyl-L-galactopyranose (a P-in-the-ring L-fucose analogue) Reviewed
T. Hanaya, K. Yasuda, H. Yamamoto, H. Yamamoto
Bulletin of the Chemical Society of Japan 66 2315 - 2322 1993
-
Synthesis of 5-Deoxy-5-hydroxyphosphinyl-D-mannopyranoses Reviewed
T. Hanaya, K. Hirose, H. Yamamoto
Heterocycles 36 2557 - 2564 1993
-
SYNTHESIS OF 2-AMINO-2,5,6-TRIDEOXY-5-PHENYLPHOSPHINYL-L-GALACTOPYRANOSE - THE P-IN-THE-RING ANALOG OF L-FUCOSAMINE Reviewed
T HANAYA, H YAMAMOTO, H KAWAMOTO, MA ARMOUR, AM HOGG, H YAMAMOTO
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 65 ( 11 ) 2922 - 2925 1992.11
-
ORIENTATION OF THE ADDITION OF DIMETHYL PHOSPHONATE TO 5,6-DIDEOXY-6-NITRO-D-HEX-5-ENOFURANOSES Reviewed
T. Hanaya, H. Yamamoto, H Yamamoto
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 65 ( 4 ) 1154 - 1156 1992.4
-
Synthesis of 2,4-Dideoxy-4-hydroxyphosphonoyl-D-erythro- and -L-threo-pentofuranoses (共著) Reviewed
T. Hanaya, A. Noguchi, M.-A. Armour, A. M. Hogg, H. Yamamoto
J. Chem. Soc. Perkin Trans. 1 295 - 301 1992
-
Preparation;Structure of Phosphono Sugar;N-Glycosides Reviewed
M. Yamashita, A. Iida, K. Ikai, T. Oshikawa, T. Hanaya, H. Yamamoto
Chem. Lett. 407 - 410 1992
-
X-RAY CRYSTAL-STRUCTURES OF 1,2,4-TRI-O-ACETYL-5-DEOXY-3-O-METHYL-5-[(S)-PHENYLPHOSPHINYL]-ALPHA-D-XYLOPYRANOSE AND ITS 5-[(S)-PHENYLPHOSPHINOTHIOYL] DERIVATIVE, AND CONFORMATIONS OF D-XYLOPYRANOSE ANALOGS HAVING A C6H5P(=R) GROUP IN THE HEMIACETAL RING Reviewed
T RICHTER, P LUGER, T HANAYA, H YAMAMOTO
CARBOHYDRATE RESEARCH 222 11 - 21 1991.12
-
AN EFFICIENT SYNTHESIS OF 2,4-DIDEOXY-4-HYDROXYPHOSPHINYL-D-ERYTHRO-PENTOFURANOSE Reviewed
T HANAYA, A NOGUCHI, H YAMAMOTO
CARBOHYDRATE RESEARCH 209 C9 - C12 1991
-
T. Hanaya, H. Yamamoto, T. Ohmae, H. Kawamoto, M.-A. Armour, A. M. Hogg, H. Yamamoto
Bull. Chem. Soc. Jpn. 64 ( 3 ) 869 - 876 1991
-
Synthesis of 6-Deoxy-4-O-methyl-6-phenylphosphinyl-D-fructopyranoses. The First P-in-the-Ring Analogs of a Ketose Reviewed
T. Hanaya, R. Okamoto, Y. V. Prikhod'ko, H. Yamamoto
Chem. Lett. 1439 - 1442 1991
-
Synthesis of 5-Deoxy-5-phenylphosphino- and 5-Phenylphosphinyl-D-glucopyranoses. Reviewed
Hanaya Tadashi, Akamatsu Akihito, Kawamoto Heizan, Armour Margaret-Ann, Hogg Alan M., Yamamoto Hiroshi
Bull. Chem. Soc. Jpn. 64 ( 8 ) 2398 - 2401 1991
-
A CONVENIENT SYNTHESIS OF (2R)-1-AMINO-1-DEOXY-1-PHOSPHINYLGLYCEROLS Reviewed
T HANAYA, A MIYOSHI, A NOGUCHI, H KAWAMOTO, MA ARMOUR, AM HOGG, H YAMAMOTO
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 63 ( 12 ) 3590 - 3594 1990.12
-
SYNTHESIS OF 5-DEOXY-3-O-METHYL-5-PHENYLPHOSPHINYL-L-FUCOPYRANOSES - THE 1ST P-IN-RING SUGAR ANALOGS OF L-FUCOSE TYPE Reviewed
T HANAYA, T OHMAE, H KAWAMOTO, H YAMAMOTO
CHEMISTRY LETTERS ( 8 ) 1359 - 1360 1990.8
-
A CONVENIENT SYNTHESIS OF 1,2,4-TRI-O-ACETYL-5-DEOXY-5-[(R)- AND (S)-ETHYLPHOSPHINO AND PHENYLPHOSPHINO]-3-O-METHYL-ALPHA,BETA-D-XYLOPYRANNOSES AND THEIR PHOSPHINOTHIOYL DERIVATIVES Reviewed
T HANAYA, N SHIGETOH, H YAMAMOTO, MA ARMOUR, AM HOGG
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 63 ( 2 ) 421 - 427 1990.2
-
Synthesis and structural analysis of 5-deoxy-5-[(R)- and (S)- methylphosphinyl]-α,β-D-manno- and -L-gulopyranoses Reviewed
T. Hanaya, K. Ohmori, H. Yamamoto, M. A. Armour, A. M. Hogg
Bull. Chem. Soc. Jpn. 63 ( 4 ) 1174 - 1179 1990
-
AN IMPROVED SYNTHESIS OF THE 5-DEOXY-5-(HYDROXYPHOSPHINYL)-D-GLUCOPYRANOSES, AND CRYSTAL-STRUCTURES OF 1,2,3,4,6-PENTA-O-ACETYL-5-DEOXY-5-[(R)-METHOXYPHOSPHINYL]-BETA-D-GLUCOPYRANOSE AND ITS 5-[(R)-ETHYLPHOSPHINYL] CONGENER Reviewed
T RICHTER, P LUGER, T HANAYA, H YAMAMOTO
CARBOHYDRATE RESEARCH 193 9 - 21 1989.10
-
SYNTHESIS OF 5-DEOXY-5-[(R AND S)-METHYLPHOSPHINYL]-ALPHA, BETA-D-MANNO-PYRANOSES - THE 1ST P-IN-RING SUGAR ANALOGS OF D-MANNOSE TYPE Reviewed
H YAMAMOTO, T HANAYA, K OHMORI, H KAWAMOTO
CHEMISTRY LETTERS ( 8 ) 1471 - 1472 1989.8
-
SYNTHESIS AND STRUCTURAL-ANALYSIS OF 4-DEOXY-4-(HYDROXYPHOSPHINYL AND PHENYLPHOSPHINYL)-D-RIBOFURANOSES Reviewed
T HANAYA, H YAMAMOTO
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 62 ( 7 ) 2320 - 2327 1989.7
-
SYNTHESIS OF 1,2,4-TRI-O-ACETYL-5-DEOXY-5-[(R,S)-ETHYL AND PHENYLPHOSPHINO]-3-O-METHYL-ALPHA,BETA-D-XYLOPYRANOSES AND AN EFFICIENT CONVERSION TO THE CORRESPONDING 5-(PHOSPHINOTHIOYL)-D-XYLOPYRANOSES Reviewed
H YAMAMOTO, T HANAYA, N SHIGETOH, H KAWAMOTO, S INOKAWA
CHEMISTRY LETTERS ( 2 ) 349 - 352 1989.2
-
AN EFFICIENT SYNTHESIS OF 4-DEOXY-4-(HYDROXYPHOSPHINYL)-D-RIBOFURANOSES - THE 1ST D-RIBOFURANOSE ANALOGS HAVING HYDROXYPHOSPHINYL GROUP IN THE HEMIACETAL RING Reviewed
H YAMAMOTO, T HANAYA, H KAWAMOTO, S INOKAWA
CHEMISTRY LETTERS 121 - 124 1989
-
Synthesis and Reaction of 2-Arylhydrazinotropones. II. Synthesis of 5-Aryltropolones and B-Ring-Open Colchicine Analogues via Benzidine Type Rearrangement of 2-(2- Arylhydrazino)tropones Reviewed
T. Nozoe, K. Takase, M. Yasunami, M. Ando, H. Saito, K. Imafuku, B.-Z. Yin, M. Honda, Y. Goto, T. Hanaya, Y. Hara, H. Yamamoto
Bull. Chem. Soc. Jpn. 62 128 - 142 1989
-
SYNTHESIS OF 2,4-DIDEOXY-4-[(S)-METHYLPHOSPHINYL]-ALPHA,BETA-D-ERYTHRO-PENTOFURANOSES AND 2,4-DIDEOXY-4-[(R)-CYCLOHEXYLPHOSPHINYL]-ALPHA,BETA-D-ERYTHRO-PENTOFURANOSES - THE 1ST P-IN-RING SUGAR ANALOGS OF 2-DEOXY-D-RIBOFURANOSE TYPE Reviewed
H YAMAMOTO, A NOGUCHI, K TORII, K OHNO, T HANAYA, H KAWAMOTO, S INOKAWA
CHEMISTRY LETTERS ( 9 ) 1575 - 1576 1988.9
-
SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-DEOXY-3-O-METHYL-5-C-[(R)-XYLDPYRANOSES AND (S)-PHENYLPHOSPHINOTHIOYL]-ALPHA AND BETA-D-XYLOPYRANOSES Reviewed
T HANAYA, N SHIGETOH, H YAMAMOTO
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 61 ( 7 ) 2499 - 2505 1988.7
-
SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-DEOXY-5-[(RS)-ETHYLPHOSPHINYL]-ALPHA,BETA-L-IDOPYRANOSES Reviewed
H YAMAMOTO, T HANAYA, H KAWAMOTO, S INOKAWA
JOURNAL OF ORGANIC CHEMISTRY 53 4790 - 4793 1988
-
SYNTHESIS AND CHARACTERIZATION OF 5-DEOXY-3-O-METHYL-5-C-[(R) AND (S)-PHENYLPHOSPHINOTHIOYL)-ALPHA-D-XYLOPYRANOSES AND BETA-D-XYLOPYRANOSES - THE 1ST SUGAR ANALOG HAVING A PHOSPHINOTHIOYL GROUP IN THE HEMIACETAL RING Reviewed
H YAMAMOTO, T HANAYA, N SHIGETOH, H KAWAMOTO, S INOKAWA
CHEMISTRY LETTERS ( 10 ) 2081 - 2084 1987
-
SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-DEOXY-5-C-(HYDROXYPHOSPHINYL)-XYLOPYRANOSE AND 5-DEOXY-5-C-(HYDROXYPHOSPHINYL)-GLUCOPYRANOSE Reviewed
H YAMAMOTO, T HANAYA, H KAWAMOTO, S INOKAWA, M YAMASHITA, MA ARMOUR, TT NAKASHIMA
JOURNAL OF ORGANIC CHEMISTRY 50 3516 - 3521 1985
-
SYNTHESIS AND THE STRUCTURAL-ANALYSIS OF 1,2,3,4-TETRA-O-ACETYL-5-DEOXY-5-C-[(R,S)-METHOXYPHOSPHINYL]-ALPHA,BETA-D-XYLOPYRANOSES Reviewed
H YAMAMOTO, T HANAYA, S INOKAWA, M YAMASHITA, MA ARMOUR, TT NAKASHIMA
CARBOHYDRATE RESEARCH 128 C5 - C8 1984
-
FORMATION AND CHARACTERIZATION OF 5-C-[(R)-(1-ACETOXY-ETHENYL)PHOSPHINYL]-1,2,4-TRI-O-ACETYL-5-DEOXY-3-O-METHYL-BETA-D-XYLOPYRANOSE Reviewed
H YAMAMOTO, T HANAYA, S INOKAWA, MA ARMOUR
Carbohydr. Res. 124 195 - 200 1983
-
Synthesis of 1,2,4-Tri-O-acetyl-5-deoxy-5-C-[(R and S)-methoxyphosphinyl]-3-O-methyl-alpha- and -beta-D-xylopyranose, and Their Structural Analysis by 400-MHz, Proton Nuclear Magnetic Resonance Spectroscopy Reviewed
H. Yamamoto, T. Hanaya, S. Inokawa, K. Seo, M.–A. Armour, T. T. Nakashima
Carbohydr. Res. 114 83 - 93 1983
Books
-
Sugar Analogs containing Carbon-Phosphorus Bonds
H. Yamamoto, T. Hanaya（Vol. 6, pp.351-384）
Studies in Natural Products Chemistry 1990
MISC
-
Synthesis of 1'-O-, 2'-O- and 1',2'-Di-O-(beta-D-glucopyranosyl)-L-biopterin Reviewed
T Hanaya, K Soranaka, H Yamamoto, W Pfleiderer
CHEMISTRY AND BIOLOGY OF PTERIDINES AND FOLATES 49 - 52 1997
-
N2-(N,N-DIMETHYLAMINOMETHYLENE)-O4-(2-P-NITROPHENYL-ETHYL)-BIOPTERIN - A VERSATILE INTERMEDIATE FOR A GLYCOSIDATION REACTION Reviewed
H. YAMAMOTO, T. HANAYA, K. TORIGOE, W. PFLEIDERER
CHEMISTRY AND BIOLOGY OF PTERIDINES AND FOLATES 21 - 24 1993
-
RECENT TOPICS IN C-P COMPOUNDS CHEMISTRY Reviewed
H YAMAMOTO, T HANAYA
NIPPON NOGEIKAGAKU KAISHI-JOURNAL OF THE JAPAN SOCIETY FOR BIOSCIENCE BIOTECHNOLOGY AND AGROCHEMISTRY 65 ( 10 ) 1518 - 1520 1991
Presentations
-
First Synthesis of a Natural Pterin Glycoside, Microcystbiopterin B
T. Hanaya, Y. Maeda, K. Iwasaki
20th European Carbohydrate Symposium (Leiden, The Netherlands) 2019
-
First Total Synthesis of a Natural Pterin Glycoside, Cyanopterin
2017
-
天然プテリングリコシドの合成研究：ソルファプテリンの合成
2016年日本化学会中国四国支部大会 2016
-
Syntheic Studies on Natural Neopterin Glycosides
23th European Colloquium on Heterocyclic Chemistry 2016
-
天然プテリングリコシドの合成研究：シアノプテリンの合成
2016年日本化学会中国四国支部大会 2016
-
1-及び3-メチルルマジン誘導体の合成研究
第30回日本プテリジン研究会 2016
-
新規ニトロキシドプローブのβ-CDによる双方向錯体形成に及ぼす特異的立体効果
2015年日本化学会中国四国支部大会 2015
-
天然プテリングリコシドの合成研究
第29回日本プテリジン研究会 2015
-
1-及び3-メチル化された天然ルマジン誘導体の合成
2015年日本化学会中国四国支部大会 2015
-
ソルファプテリンの合成研究
2015年日本化学会中国四国支部大会 2015
-
シアノプテリンの合成研究：グリコシル供与体部の合成
2015年日本化学会中国四国支部大会 2015
-
L-イジトールの新規合成と抗生物質FR-33289合成への応用
2014年日本化学会中国四国支部大会 2014
-
1-及び3-メチルルマジン誘導体の合成研究
2014年日本化学会中国四国支部大会 2014
-
シアノプテリンの合成研究：6-ヒドロキシメチルプテリンのグリコシル化
2014年日本化学会中国四国支部大会 2014
-
L-イジトールの合成とホスホン酸抗生物質FR-33289合成への応用
第４回リン化合物討論会 2013
-
天然ネオプテリングリコシドの合成研究
第27回日本プテリジン研究会 2013
-
シアノプテリンの合成研究：グリコシル供与体部の合成
2012年日本化学会西日本大会 2012
-
ネオプテリングリコシドの合成研究
2012年日本化学会西日本大会 2012
-
6-置換及び7-置換プテリン誘導体の選択的合成
2012年日本化学会西日本大会 2012
-
First Synthesis of a Natural Isoxanthopterin Glycoside, Asperopterin-A
15th International Symposium on Pteridines and Folates 2012
-
N-アセチル-D-グルコサミン型ホスファ糖の合成
2012年日本化学会西日本大会 2012
-
D-グルコサミン型ホスファ糖の合成研究
2011年日本化学会西日本大会 2011
-
シアノプテリンの合成研究
2011年日本化学会西日本大会 2011
-
環状ヒドロキサム酸構造を有する抗生物質SF-2312の合成と構造決定
第３回リン化合物討論会 2011
-
D-グルコサミン構造を有するホスファ糖の合成研究
第３回リン化合物討論会 2011
-
アスペロプテリン-Aの合成
第25回日本プテリジン研究会 2011
-
ホスホン酸型抗生物質SF-2312の合成研究と構造決定
2011年日本化学会西日本大会 2011
-
天然ネオプテリングリコシド類の合成研究
2010年日本化学会西日本大会 2010
-
ホスホン酸型抗生物質ホスホノトリキシンの合成研究
2010年日本化学会西日本大会 2010
-
ホスホン酸型抗生物質SF-2312の合成研究
2010年日本化学会西日本大会 2010
-
6-ヒドロキシメチルプテリングリコシドの合成研究
第1回日本プテリジン研究会 2010
-
環式ヒドロキサム酸構造を有する抗生物質SF-2312の合成研究
第29回C−P化合物研究会 2009
-
First Synthesis of a Representative, Natural Pterin Glycoside: 2’-O-(α-D-glucopyranosyl)biopterin
14th International Symposium on Pteridines and Folates 2009
-
ビオプテリン α-D-グルコシドの合成研究
第23回Japan Pteridine Conference, 第17回Cytokine Neopterin Meeting連合研究発表会 2009
-
ネオプテリングリコシドの合成研究
2009年日本化学会西日本大会 2009
-
6-ヒドロキシメチルプテリングリコシドの合成研究
2009年日本化学会西日本大会 2009
-
ビオプテリングリコシドの合成研究
第29回C−P化合物研究会 2009
-
ビオプテリン α-D-グルコシドの合成
2008年日本化学会西日本大会 2008
-
アスペロプテリンA,Bの合成
2008年日本化学会西日本大会 2008
-
ホスホマシシン誘導体の新規合成
2008年日本化学会西日本大会 2008
-
ビオプテリングリコシドの合成
第38回複素環化学討論会 2008
-
シリアプテリングリコシドの合成研究
第21回Japan Pteridine Conference, 第15回Cytokine Neopterin Meeting連合研究発表会 2008
-
Efficient Total Syntheses of Natural Pterin Glycosides: Limipterin and Tepidopterin
23rd European Colloquium on Heterocyclic Chemistry 2008
-
ホスホマイシン誘導体の新規合成
第28回C－P化合物研究会 2007
-
プテリングリコシド（リミプテリン、テピドプテリン）の合成研究
日本化学会第87春季年会 2007
-
D-リボフラノース及び2-デオキシ-D-リボフラノース型ホスファ糖の合成研究
日本化学会第87春季年会 2007
-
L-threo-ビオプテリングリコシド（テピドプテリン）の合成研究
第21回Japan Pteridine Conference, 第15回Cytokine Neopterin Meeting連合研究発表会 2007
-
L-threo-ビオプテリングリコシド類の合成
2007年日本化学会西日本大会 2007
-
2-デオキシ-D-リボフラノース型ホスファ糖の新規合成
2007年日本化学会西日本大会 2007
-
アルキル置換およびベンゾアズレン類の合成
2007年日本化学会西日本大会 2007
-
An Efficient, Selective Synthesis of 1'-O- and 2'-O-(b-D-glucopyranosyl)-L-biopterin and Limipterin
2nd International Conference on Heterocyclic Chemistry 2006
-
Synthetic Studies on Phospholane Oxides and Phosphorinane Oxides Having Oxygen Functional Groups
2nd International Conference on Heterocyclic Chemistry 2006
-
1'-O-及び2'-O-グリコシル-L-ビオプテリンの選択的合成
第20回Japan Pteridine Conference, 第14回Cytokine Neopterin Meeting連合研究発表会 2006
-
ビオプテリングリコシドの選択的合成
2006年日本化学会西日本大会 2006
-
アルキル置換アズレン類の合成研究
2006年日本化学会西日本大会 2006
-
D-フルクトピラノース骨格を有するホスファ糖、チオ糖、イミノ糖の合成
第27回Ｃ－Ｐ化合物研究会 2005
-
スクロースを用いたD-フルクトフラノース誘導体の合成とヘテロ糖合成への応用
2005年日本化学会西日本大会 2005
-
部分的に保護された新規L-ビオプテリン誘導体の合成とグリコシル化
2005年日本化学会西日本大会 2005
-
1,2-ジヒドロキシプロピル側鎖を有するプテリジン誘導体の新規合成
2005年日本化学会西日本大会 2005
-
D-グルコサミンの環内にリン原子を有するホスファ糖の合成研究
2005年日本化学会西日本大会 2005
-
トロピリデンを母体とする炭素数１２の多環状ポリエノンの合成
2005年日本化学会西日本大会 2005
-
側鎖水酸基を部分的に保護したL-ビオプテリン誘導体の合成とグリコシル化
第19回Japan Pteridine Conference 2005
-
アミノ置換基を有するジヒドロアズレノン類の合成研究
2004年日本化学会西日本大会 2004
-
スクロースを用いたD-フルクトフラノース誘導体の合成
2004年日本化学会西日本大会 2004
-
２－デオキシ-D-リボフラノース型ホスファ糖の合成
2004年日本化学会西日本大会 2004
-
電解還元反応を用いる三環式化合物の合成研究
2004年日本化学会西日本大会 2004
-
ジメチルジヒドロアズレノンの合成と反応
2003年日本化学会西日本大会 2003
-
D-フルクトピラノース骨格を有するホスファ糖の合成
2003年日本化学会西日本大会 2003
-
５－ホスフィニルヘキソフラノースの５位水酸基の脱酸素化の立体選択性
第２５回Ｃ－Ｐ化合物研究会 2002
-
５－ホスフィニルヘキソフラノース誘導体の５位水酸基の脱酸素化の立体選択性
２００２年日本化学会西日本大会 2002
-
ビオプテリンのグリコシド誘導体：天然物及び類似体の合成研究
第２５回Ｃ－Ｐ化合物研究会 2002
-
1Ｃ4立体配座を優先するリン糖誘導体の合成と構造解析
第２５回Ｃ－Ｐ化合物研究会 2002
-
リミプテリンの合成研究
２００２年日本化学会西日本大会 2002
-
N-Arylacetyl-N'-[3-(2-pyridyldithio)propanoyl]-alpha,omega-alkanediamineの合成研究
２００２年日本化学会西日本大会 2002
-
モノ及びジメトキシジヒドロアズレノン類の合成研究
２００２年日本化学会西日本大会 2002
-
電解還元反応によるビシクロケトン類の合成研究
日本化学会中国四国支部・同九州支部合同大会 2001
-
α－ヒドロキシホスホネートの脱ヒドロキシル化の立体選択性とホスファ糖合成への応用
日本化学会第７９春季年会 2001
-
ピラノース環内にリン原子を有するＤ－ガラクトトース誘導体の合成
日本化学会中国四国支部・同九州支部合同大会 2001
-
α－ヒドロキシホスホネート誘導体の脱ヒドロキシル化によるＤ－マンノース型リン糖の合成研究
日本化学会中国四国支部・同九州支部合同大会 2001
-
1'-O-グリコシル L-ビオプテリン誘導体の合成研究
日本化学会中国四国支部・同九州支部合同大会 2001
-
芳香族アミノジアゾケトン類のRh触媒による分解反応
日本化学会中国四国支部・同九州支部合同大会 2001
-
ビオプテリンのグリコシド誘導体：天然物および類似体の合成研究
第２４回Ｃ－Ｐ化合物研究会 2000
-
Phospha-sugars: A Pseudo-sugar having a Phosphorus Atom in the Hemiacetal Ring
8th International Symposium on Natural Product Chemistry 2000
-
α－ヒドロキシホスホネートの脱酸素化の選択性とリン糖合成への応用
第２４回Ｃ－Ｐ化合物研究会 2000
-
1Ｃ4立体配座を有する新規リン糖誘導体の合成と構造解析
日本化学会第７７秋季年会 1999
-
フラノース環内にリン原子を有するＤ－リボフラノース誘導体の改良的合成
日本化学会第７６春季年会 1999
-
アミノアズレン誘導体の合成研究
日本化学会第７６春季年会 1999
-
Synthetic Studies of D-ribofuranose Analogs Having a Phosphorus Atom in the Hemiacetal Ring
17th International Congress of Heterocyclic Chemistry 1999
-
ピラノース環内にリン原子を有する糖類似体（リン糖）の合成と構造解析
第１４回若手化学者のための化学道場 1998
-
５－デオキシ－５－ヒドロキシホスフィニル－Ｄ－ガラクトピラノース誘導体の合成
日本化学会第７５秋季年会 1998
-
Synthetic Studies of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring
17th European Colloquium on Heterocyclic Chemistry 1998
-
Ｄ－ガラクトピラノース型リン糖の合成
第２３回Ｃ－Ｐ化合物研究会 1998
-
リン原子を有するピラノース環のビシナル1H－1H結合へ及ぼすリン原子の効果
第２３回Ｃ－Ｐ化合物研究会 1998
-
２－アミノ－２，５－ジデオキシ－５－ヒドロキシホスフィニル－Ｄ－マンノピラノース誘導体（マンノサミン型リン糖）の合成
日本化学会第７４春季年会 1998
-
Synthesis of 1'-O-, 2'-O- and 1',2'-Di-O-(b-D-glucopyranosyl)-L-biopterin
11th International Symposium on Chemistry and Biology of Pteridines and Folates 1997
-
リン原子を有するピラノース誘導体におけるリン原子のビシナル1H－1H結合定数への影響（リン原子の置換基効果の加成則）
日本化学会第７２春季年会 1997
-
トロピリデン環を有するジアゾケトンを用いた多環状ポリエノンの合成
日本化学会第７２春季年会 1997
Research Projects
-
Development of New Cross-Couplings Catalyzed by Group IX Metals.
Grant number：20550043 2008 - 2010
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)
NISHIHARA Yasushi, HANAYA Tadashi, SUEISHI Yoshimi
Grant amount：\4810000 （ Direct expense: \3700000 、 Indirect expense：\1110000 ）
Catalytic cross-coupling between carbon electrophiles andorganometallic nucleophiles is one of the most useful method to construct carbon-carbonbonds in organic synthesis. In this research, group 9 metals were used as the catalyst in place of conventional group 10 metals like nickel and palladium, intending to open new areas of cross-coupling.
As the results, two methods were developed, where, by the catalysis with rhodium, otherwise difficult cross-couplings between alkyl electrophiles and arylzinc nucleophiles successfully take place. The Rh catalysts also achieved unprecedented cross-couplingreactions between arylzinc compounds and unsaturated molecules like carbon monoxideand alkenes by the assistance of oxidants. -
Studies on Synthesis of Phospha-sugars by a New Route and Their Enzyme Inhibition
Grant number：10640521 1998 - 1999
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)
HANAYA Tadashi, YAMAMOTO Hiroshi
Grant amount：\2800000 （ Direct expense: \2800000 ）
A New Route for Preparation of Pyranose-type Phospha-sugars.
D-gluco and L-idopyranose phospha-sugars were prepared in 6 steps, by starting with 3, 6-di-O-benzyl-1, 2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose.
2. Synthesis of D-Galactopyranose Phospha-sugar.
D-galactopyranose phospha-sugar was prepared in 6 steps, by starting with 3, 6-di-O-benzyl-1, 2-O-isopropylidene-β-L-arabino-hexofuranos-5-ulose.
3. Synthesis of D-mannosamine Phospha-sugar.
3, 6-Di-O-benzyl-5-O-deoxy-5-dimethylphosphinyl-1,2 O-isopropylidene-α-D-glucofuranose was converted, in 4 steps, into methyl 2-acetamido-3, 6-di-O-benzyl-2, 5-dimethoxyphosphinyl-α-D-mannofuranoside, which led to 3, 5-di-O-benzyl derivatives of D-mannosamine phospha-sugar.
4. The effect of a Phosphorus Atom upon Vicinal ィイD11ィエD1H-ィイD11ィエD1H Coupling Constants in Phospha-sugars.
Additivity constants for phosphorus were estimated for the prediction of vicinal ィイD11ィエD1H-ィイD11ィエD1H coupling constants by means of an additivity rule in a series of pyranose-type phospha-sugars. -
EFFICIENT CHEMICAL SYNTHESIS OF NATURAL PTERIN DERIVATIVES
Grant number：07045016 1995 - 1997
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for international Scientific Research
YAMAMOTO Hiroshi, HANAYA Tadashi, PFLEIDERER Wolfgang
Grant amount：\2400000 （ Direct expense: \2400000 ）
1. Detaild investigation of a convenient and preparative synthetic scheme for N2- (N,N-dimethyl-aminomethylene) -3- (p-nitrophenethyl) -biopterin, its dihydro and tetrahydro derivatives. [1] 1'-and 2'-beta-D-Glucopyranosyl derivatives were efficiently obtained by employing the above-mentioned N2, N3-protected biopterin a key intermediate, which was successively tetramethylsilylated and then subjected to glycosylation in dichloromethane in presence of stannic chloride. Use of 2.5 equivalent mole of glycosyl donor conveniently afforded the 1', 2'-di-O-glucosyl derivative. [2] Similarly obtained was the 2'-O-beta-D-ribofuranosyl biopterin derivative in a relatively high overall yield. [3] A natural product limipterin {2'-O-beta-D- (N-acetylglucosaminyl) -biopterin} was efficiently synthesized in a similar manner by employing 1,3,4,5-tetra-O-acetyl-2-N- (N,N-phthaloyl) -beta-D-glucosamine as the sugar donor. [4] Catalytic hydrogenation of these N2- (N,N-dimethylaminomethylene) -3- (p-nitrophenethyl) -biopterin in ethyl acetate in the presence of platinum conveniently afforded their tetrahydro derivatives as the main products, suggesting that the present synthetic scheme would be useful in preparation of a series of glycosylated biopterins.
2,3. Chemical synthesis of sepiapterin and its derivatization by selective glycosylation and alkylation, as well as overall and detailed structure-activity relationship of biopterin derivatives are currently under intensive study. Physiological assay of the above-mentioned newly abtained products is also in progress. -
新規リン糖及びリン糖誘導体の合成と生理活性
Grant number：05640609 1993
日本学術振興会 科学研究費助成事業 一般研究(C)
山本 啓司, 花谷 正
Grant amount：\2000000 （ Direct expense: \2000000 ）
1.リン酸ヌクレオシドの合成研究:リン糖モノマーをヌクレオシドやグリコシドに導くためのC-1のOH基活性化検討の目的で、入手しやすいモデル化合物としてD-マニトール及びL-リンゴ酸からそれぞれ(2R)-2,3-O-イソプロピリデン-1-ホスフィニルグリセロール及び(3S)-3,4-O-イソプロピリデン-1-ホスフィニルテトリトールを合成した。これらの1-OHをメシレートあるいはトリフレートによって活性化し、アルキルアミノ基やアジド基に変換できた。さらに収率はまだ低いがアデニルも導入できることが判明した。現在D-リボフラノスース型及び2-デオキシ-D-リボフラノース型リン糖のC-1活性モノマー調製を行っており、ついで基本的な塩基との縮合反応によりリン糖ヌクレオシドの合成を行なう。2.リン糖グリコシドの合成研究:D-キシロピラノースおよびD-グルコピラノースのC-1活性モノマー(O-メシレート、トリフレート、ブロモ誘導体)の調製を検討したが、2〜6-OHの最適な保護基の選択的導入、脱離の問題が、まだ完全に解決していない。この点がクリアーできれば、グリコシル化は容易と考えられ、鋭意検討中である。3.新規リン糖モノマー合成研究:コハク酸より導かれる1,4-ジブロモ-2,3-ジメトキシブタンをフェニルホスホニルジクロリド存在下グリニアール反応を利用して、効率的な環化を行い、次いで環リン原子のα位をカルバニオンにして、種々の置換基を導入することにより、新規経路によるリン糖合成を行っている。また、D-グルコースを出発原料として、6-アミノ-D-グルコース型リン糖合成に成功した。D-フルクトース型、L-フコース及びフコサミン型リン糖モノマーも合成された。現在、2-N-アセチルグルコサミン型リン糖が完成しつつある。4.上記合成の中間体及び生成物の生物活性については順次テストしている。
-
Studies and physiological activity of glycosides of biopterin and related pteridienes
Grant number：03045035 1991 - 1993
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for international Scientific Research
YAMAMOTO Hiroshi, HANAYA Tadashi, PFLEIDERER W.
Grant amount：\2100000 （ Direct expense: \2100000 ）
A certain number of pteridines having a glycosidated side-chain occur in nature. Moreover, glycosides of biopterin and related pteridines are considered to be of interest in view of potent biological activities. Thus, we have explored efficient and versatile glycosidation methods of biopterin and found that an N^2,N(3)-protected biopterin can conveniently be subjected to various reactions including glycosidation.
The reaction of biopterin with N,N-dimethylformamide diethylacetal in DMF at 20ﾟC gave N^2-(N,N-dimethylaminomethylene)-biopterin, which was then converted into the 1',2'-di-O-acetyl derivative. This was led by Mitsunobu reaction to the 3-NPE-biopterin derivative [NPE = p-nitrophenethyl], which, upon methanolysis at 50ﾟC, furnished versatile N^2,N(3)- protected biopterin (PB). This compound is soluble in various nonpolar aprotic solvents and can be subjected to a variety of the diol reactions of the side-chain.
Glycosidation of PB (via di-O-trimethylsilylated PB) was studied by employing 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose as a model substrate, thus affording a mixture of N^2,N(3)-protected biopterin-2'-O-beta-D- ribofuranoside and -1',2'-di-O-beta-D-ribofuranoside, the yields of which depended upon the molar ratio of the sugar donor to PB. Deprotection of these ribosides was performed stepwise. The N(3)-NPE group was cleaved by the action of DBU in DMF, whereas debenzoylation and deamidination were effected by treatment respectively with sodium methoxide in methanol and aqueous methanolic ammonia, thus affording biopterin-2'-O-beta-D-ribofuranoside and -1',2'-di-O-beta-D-ribofuranoside.
Similar results were obtained for glycosidation using a glucopyranose donor to afford biopterin-2'-O-and -1'-O-beta-D-glucopyranoside. Deprotection steps of these glucoside, as well as biological assays of all glycosides obtained, are in progress. -
オリゴリン糖及びリン糖ヌクレオシドの合成と生理活性
Grant number：63540400 1988
日本学術振興会 科学研究費助成事業 一般研究(C)
山本 啓司, 花谷 正
Grant amount：\1600000 （ Direct expense: \1600000 ）
1.4-デオキシ-4-C-ホスフィニル-D┣=┫-リボフラノース類の、より効率的かつ大量調製に適した合成方法につき研究を行い、従来得られていた4-C-(エチルホスフィニル)体の収率向上が実現しただけでなく、4-C-(ヒドロキシおよびフェニルホスフィニル)体も効率よく得られるようになった。また選択的にD-リボフラノース型化合物が得られる反応機構についても大体の解明がなされ、今後これらの化合物の調製法を考慮する際に大いに役に立つ情報が得られた。さらに2-デオキシ-D-リボ型リン糖も、未だ収率向上と合成段階短縮の余地は残されているが、2,4-ジデオキシ-4-C-(メチルおよびシクロヘキシル)-D-エリトロ-ペントフラノースが始めて合成できた。このようにして合成されたD-リボフラノース体のC-1位のOH基あるいはアセトキシ基をブロム体等の活性原子に変換する試みを数多く行ったが、環内に酸素原子を持つ糖類とかなり異り、置換反応を起しにくいことが分った。しかし、1-ジメチルホスフィニル-2、3-O-イソプロピリデン-D-グリセロールを用いたモデル実験で、塩化チオニルあるいは四塩化炭素-トリフェニルホスフィンを用いると1位の水酸基がクロル原子に置換することが判明した。この方法を現在上記D-リボ型リン糖に応用し検討している所である。
2.5-デオキシ-5-C-(ヒドロキシホスフィニル)-D-グルコピラノース合成の全段階通算収率が以前のものより2倍に向上した改良法、5-デオキシ-5-C-(エチルホスフィニル)-L-イドピラノースの選択的合成法、および環内にP=S結合を含むリン糖として5-デオキシ-5-(エチルおよびフェニルホスフィノチオイル)-D-キシロピラノース合成法を始めて開発した。これらのC-1位の活性化並びに得られた種々のリン糖の生理活性については現在検討中である。
Class subject in charge
-
Introduction to Information Processing 1 （2025academic year） 1st semester - 月3～4
-
Advanced Reaction Chemistry （2024academic year） Late - 木1～2
-
Introduction to Information Processing 1 （2024academic year） 1st semester - 月3,木3
-
Organic Synthesis （2024academic year） 3rd and 4th semester - 水3～4
-
Organic Synthesis 1 （2024academic year） Third semester - 水3～4
-
Organic Synthesis 2 （2024academic year） Fourth semester - 水3～4
-
Advanced Reaction Chemistry （2023academic year） Late - 木1～2
-
Synthetic Carbohydrate Chemistry （2023academic year） Late - その他
-
Heterocyclic Chemistry of Natural Products （2023academic year） Late - 木1～2
-
Introduction to Information Processing 1 （2023academic year） 1st semester - 月3,木3
-
Organic Synthesis （2023academic year） 3rd and 4th semester - 水3～4
-
Seminar in Organic Synthetic Chemistry （2023academic year） Year-round - その他
-
Organic Synthesis 1 （2023academic year） Third semester - 水3～4
-
Organic Synthesis 2 （2023academic year） Fourth semester - 水3～4
-
Advanced Reaction Chemistry （2022academic year） Late - 木1～2
-
Synthetic Carbohydrate Chemistry （2022academic year） Late - その他
-
Introduction to Information Processing 1 （2022academic year） 1st semester - 月3,木3
-
Organic Chemistry 10 （2022academic year） Fourth semester - 月1～2
-
Organic Chemistry 9 （2022academic year） Third semester - 月1～2
-
Organic Chemistry Ⅳ （2022academic year） 3rd and 4th semester - 月1～2
-
Seminar in Organic Synthetic Chemistry （2022academic year） Year-round - その他
-
Organic Synthesis 1 （2022academic year） Third semester - 水3～4
-
Organic Synthesis 2 （2022academic year） Fourth semester - 水3～4
-
Synthetic Carbohydrate Chemistry （2021academic year） Late - その他
-
Heterocyclic Chemistry of Natural Products （2021academic year） Late - 金1,金2
-
Introduction to Information Processing 1 （2021academic year） 1st semester - 月3,木3
-
Organic Chemistry 7 （2021academic year） Third semester - 月1,月2
-
Organic Chemistry 8 （2021academic year） Fourth semester - 月1,月2
-
Organic Synthesis 1 （2021academic year） Third semester - 水3,水4
-
Organic Synthesis 2 （2021academic year） Fourth semester - 水3,水4
-
Introduction to Natural Science 2(Chemistry) （2021academic year） Second semester - 火3,火4
-
Synthetic Carbohydrate Chemistry （2020academic year） Late - その他
-
Heterocyclic Chemistry of Natural Products （2020academic year） Late - 金1,金2
-
Introduction to Information Processing 1 （2020academic year） 1st semester - 月3,木3
-
Organic Chemistry 7 （2020academic year） Third semester - 月1,月2
-
Organic Chemistry 8 （2020academic year） Fourth semester - 月1,月2
-
Organic Chemistry Ⅳ （2020academic year） 3rd and 4th semester - 月1,月2
-
Organic Synthesis （2020academic year） 3rd and 4th semester - 水3,水4
-
Organic Synthesis 1 （2020academic year） Third semester - 水3,水4
-
Organic Synthesis 2 （2020academic year） Fourth semester - 水3,水4