SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)

被引：0

作者：

FRICK, W ^{[1
]}

KRULLE, T ^{[1
]}

SCHMIDT, RR ^{[1
]}

机构：

[1] UNIV CONSTANCE,FAK CHEM,POSTFACH 5560,W-7750 CONSTANCE,GERMANY

来源：

LIEBIGS ANNALEN DER CHEMIE | 1991年 / 05期

关键词：

PHOSPHONIUM BROMIDE; (BENZYLOXY)(BENZYLOXYCARBONYL)METHYL]TRIPHENYL; WITTIG REACTION; D-MANNOSE ALDEHYDE; SYNTHESIS OF PER-0-PROTECTED; KDO, SYNTHESIS OF 4,5-7,8-DI-0-ISOPROPYLIDENE-PROTECTED;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide (8), obtained from glyoxylic acid via a convenient one-pot procedure, reacted in a Wittig reaction with 4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannose (7), readily synthesized on a large scale from D-mannose, to provide the KDO derivative 9. Hydrogenolytic removal of the benzyl groups furnished directly the 4,5:7,8-di-O-isopropylidene protected KDO 11. Its treatment with diazomethane led to the known ester derivative 12-alpha, beta (2:1 anomeric mixture) which could be also obtained by transesterification of 9 and subsequent hydrogenolytic debenzylation.

引用

页码：435 / 438

页数：4

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