Mannuronolactone acetonide:: easy access to C-3 OH and C-5 OH of mannose

被引：2

作者：

Watterson, MP

Martin, A

Krülle, TM

Estevez, JC

Fleet, GWJ

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Univ Santiago de Compostela, Fac Ciencias, Dept Quim Organ, Santiago De Compostela 15706, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(97)00604-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of D-mannuronolactone acetonide 1 is described from alginic acid and provides an efficient route for the manipulation at C-5 of mannose. Reduction gives a new acetonide of mannose, 1,2-O-isopropylidene-beta-D-mannofuranose which, on further acetonation, gives 1,2:5,6-di-O-isopropylidene-beta-D-mannofuranose [giving easy access to C-3 OH of mannose] together with a small amount of 1,2:3,5-di-O-isopropylidene-beta-D-mannofuranose. Some silylated derivatives of mannuronolactone allow immediate access to the C-6 of mannose. Such intermediates are likely to be of value in the synthesis of derivatives of mannose. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：4111 / 4120

页数：10

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