PREPARATION OF 2-O-(3-O-CARBAMOYL-ALPHA-D-MANNOPYRANOSYL)-L-GULOPYRANOSE - SYNTHETIC STUDY ON THE SUGAR MOIETY OF ANTITUMOR ANTIBIOTIC BLEOMYCIN

被引：11

作者：

OSHITARI, T ^{[1
]}

KOBAYASHI, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 07期

关键词：

D O I：

10.1016/0040-4039(94)02458-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new practical route to the disaccharide moiety of bleomycin was developed. Both of key building blocks 9 and 16 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of the allyl alcohol 9 with the trichloroacetimidate 16 proceeded smoothly, and the further incorporation to the disaccharide moiety was successfully accomplished.

引用

页码：1089 / 1092

页数：4

共 50 条

[21] SYNTHESIS OF THE 1,2'-1',2-DIANHYDRIDE OF 3,4-DI-O-ACETYL-BETA-L-RHAMNOPYRANOSE AND METHYL 3,4-DI-O-ACETYL-ALPHA-D-GALACTOPYRANURONATE FROM "2-O-(ALPHA-D-GALACTOPYRANOSYLURONIC ACID)-L-RHAMNOPYRANOSE
FUJIWARA, T
ARAI, K
CARBOHYDRATE RESEARCH, 1979, 69 (MAR) : 107 - 115
[22] SYNTHETIC STUDIES ON AN ANTITUMOR ANTIBIOTIC BLEOMYCIN .25. AN EFFICIENT SYNTHESIS OF ERYTHRO-BETA-HYDROXY-L-HISTIDINE, THE PIVOTAL AMINO-ACID OF BLEOMYCIN-FE(II)-O2 COMPLEX
OWA, T
OTSUKA, M
OHNO, M
CHEMISTRY LETTERS, 1988, (11) : 1873 - 1874
[23] SYNTHETIC STUDIES ON AN ANTITUMOR ANTIBIOTIC, BLEOMYCIN .21. ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-HYDROXY-L-HISTIDINE, THE PIVOTAL AMINO-ACID OF BLEOMYCIN-FE(II)-O2 COMPLEX
OWA, T
OTSUKA, M
OHNO, M
CHEMISTRY LETTERS, 1988, (01) : 83 - 86
[24] A Gene Cluster for Biosynthesis of Mannosylerythritol Lipids Consisted of 4-O-β-D-Mannopyranosyl-(2R, 3S)-Erythritol as the Sugar Moiety in a Basidiomycetous Yeast Pseudozyma tsukubaensis
Saika, Azusa
Koike, Hideaki
Fukuoka, Tokuma
Yamamoto, Shuhei
Kishimoto, Takahide
Morita, Tomotake
PLOS ONE, 2016, 11 (06):
[25] C-13-NMR STUDY OF METHYL-ETHER AND BENZYL-ETHER OF L-ARABINOSE AND OLIGOSACCHARIDES HAVING L-ARABINOSE AT THE REDUCING END - SYNTHESIS OF 2-O-BETA-D-GLUCOPYRANOSYL-L-ARABINOSE 2-O-ALPHA-L-RHAMNOPYRANOSYL-, 3-O-BETA-D-GLUCOPYRANOSYL-2-O-ALPHA-L-RHAMNOPYRANOSYL-L-ARABINOSE AND 4-O-BETA-D-GLUCOPYRANOSYL-2-O-ALPHA-L-RHAMNOPYRANOSYL-L-ARABINOSEIN
LIPTAK, A
SZURMAI, Z
NANASI, P
NESZMELYI, A
TETRAHEDRON, 1982, 38 (23) : 3489 - 3497
[26] SYNTHETIC STUDIES IN CARBOHYDRATES .56. SYNTHESIS OF O-ALPHA-L-FUCOPYRANOSYL-(1-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE (N-ACETYL-3'-O-ALPHA-L-FUCOPYRANOSYLLACTOSAMINE)
DUBEY, R
REYNOLDS, D
ABBAS, SA
MATTA, KL
CARBOHYDRATE RESEARCH, 1988, 183 (02) : 155 - 162
[27] SYNTHETIC STUDIES IN CARBOHYDRATES .13. SYNTHESIS OF PHENYL O-ALPHA-L-FUCOPYRANOSYL-(1-]2)-O-BETA-D-GALACTOPYRANOSYL-(1-]3)-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE
RANA, SS
BARLOW, JJ
MATTA, KL
CARBOHYDRATE RESEARCH, 1980, 87 (01) : 99 - 105
[28] BRANCHED-CHAIN GLYCOSYL ALPHA-AMINO-ACIDS .1. STEREOSPECIFIC SYNTHESIS OF 2-L-(3-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOS-3-YL)GLYCINE, AN ANALOG OF POLYOXIN SUGAR MOIETY
ROSENTHAL, A
SHUDO, K
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26): : 4391 - 4395
[29] SYNTHETIC STUDIES ON OLIGOSACCHARIDE OF A GLYCOLIPID FROM THE SPERMATOZOA OF BIVALVES .2. SYNTHESIS OF A PRECURSOR OF 3-O-(2-ACETAMIDO-2-DEOXY-3-O-METHYL-ALPHA-D-GALACTOPYRANOSYL)-4-O-(4-O-METHYL-BETA-D-GLUCOPYRANOSYLURONIC ACID)-L-FUCOSE
KANIE, O
TAKEDA, T
OGIHARA, Y
CARBOHYDRATE RESEARCH, 1989, 190 (01) : 53 - 64
[30] SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .60. SYNTHESIS OF A FULLY PROTECTED DERIVATIVE OF O-(N-ACETYL-ALPHA-D-NEURAMINYL)-(2-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]3)-O-[(N-ACETYL-ALPHA-D-NEURAMINYL)-(2-]6)]-O-(2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSYL)-(1-]3)-L-SERINE
IIJIMA, H
OGAWA, T
CARBOHYDRATE RESEARCH, 1989, 186 (01) : 107 - 118

← 1 2 3 4 5 →