Novel synthesis of L-iduronic acid using trehalose as the disaccharidic starting material

被引：33

作者：

Hinou, H ^{[1
]}

Kurosawa, H ^{[1
]}

Matsuoka, K ^{[1
]}

Terunuma, D ^{[1
]}

Kuzuhara, H ^{[1
]}

机构：

[1] Saitama Univ, Fac Engn, Dept Funct Mat Sci, Urawa, Saitama 3388570, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 08期

关键词：

conformation; diastereoselection; elimination reaction; oxidation;

D O I：

10.1016/S0040-4039(98)02662-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For the preparation of L-iduronic acid, trehalose was converted into a derivative of a novel disaccharide, beta-L-idopyranosyl beta-L-idopyranoside, through diastereoselective hydroboration of the 5, 5'-di-eno intermediate. The 6- and 6'-hydroxy groups were then oxidized in two steps to give a disaccharide composed of 2 units of L-iduronate moieties, which underwent acidic cleavage of the glycosidic bond to give the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1501 / 1504

页数：4

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