ENANTIOSPECIFIC SYNTHESES OF VALIOLAMINE AND ITS (1R), (2R), (1R,2R) DIASTEREOMERS FROM (-)-QUINIC ACID

被引：30

作者：

SHING, TKM

WAN, LH

机构：

[1] Department of Chemistry, The Chinese University of Hong Kong Shatin

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 15期

关键词：

AMINOSUGARS; ASYMMETRIC SYNTHESES; DIHYDROXYLATIONS; QUINIC ACID; VALIOLAMINE;

D O I：

10.1002/anie.199516431

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Applicable also for other pseudosugars, the simple reaction sequence for the preparation of α‐D‐glucosidase inhibitors valiolamine (1) and its three diastereoisomers starts with 1,3,4,5‐tetrahydroxycyclohexanecarboxylic acid (quinic acid). Glycosidase inhibitors like 1 are used as chemotherapeutics, for example, against HIV. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1643 / 1645

页数：3

共 26 条

[1] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS
COREY, EJ
WINTER, RAE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) : 2677 - &
[2] INHIBITION OF HIV REPLICATION BY AMINO-SUGAR DERIVATIVES
FLEET, GWJ
KARPAS, A
DWEK, RA
FELLOWS, LE
TYMS, AS
PETURSSON, S
NAMGOONG, SK
RAMSDEN, NG
SMITH, PW
SON, JC
WILSON, F
WITTY, DR
JACOB, GS
RADEMACHER, TW
[J]. FEBS LETTERS, 1988, 237 (1-2) : 128 - 132
[3] FLEET GWJ, 1988, NATURAL PRODUCT ISOL, P540
[4] SYNTHESIS OF A BRANCHED-CHAIN INOSOSE DERIVATIVE, A VERSATILE SYNTHON OF N-SUBSTITUTED VALIOLAMINE DERIVATIVES FROM D-GLUCOSE
FUKASE, H
HORII, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3642 - 3650
[5] VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE
GAO, Y
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) : 7538 - 7539
[6] NOVEL SYNTHESIS OF PENTA-N,O-ACETYLVALIOLAMINE
HAYASHIDA, M
SAKAIRI, N
KUZUHARA, H
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (01) : 83 - 94
[7] STUDIES ON VALIDAMYCINS, NEW ANTIBIOTICS .6. VALIDAMINE, HYDROXYVALIDAMINE AND VALIDATOL, NEW CYCLITOLS
HORII, S
IWASA, T
MIZUTA, E
KAMEDA, Y
[J]. JOURNAL OF ANTIBIOTICS, 1971, 24 (01) : 59 - &
[8] SYNTHESIS AND ALPHA-D-GLUCOSIDASE INHIBITORY ACTIVITY OF N-SUBSTITUTED VALIOLAMINE DERIVATIVES AS POTENTIAL ORAL ANTIDIABETIC AGENTS
HORII, S
FUKASE, H
MATSUO, T
KAMEDA, Y
ASANO, N
MATSUI, K
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) : 1038 - 1046
[9] STEREOSELECTIVE CONVERSION OF VALIENAMINE AND VALIDAMINE INTO VALIOLAMINE
HORII, S
FUKASE, H
KAMEDA, Y
[J]. CARBOHYDRATE RESEARCH, 1985, 140 (02) : 185 - 200
[10] OLIGOSACCHARIDE MODIFICATION BY SWAINSONINE TREATMENT INHIBITS PULMONARY COLONIZATION BY B16-F10 MURINE MELANOMA-CELLS
HUMPHRIES, MJ
MATSUMOTO, K
WHITE, SL
OLDEN, K
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (06) : 1752 - 1756

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