New accesses to L-iduronyl synthons

被引：67

作者：

Lubineau, A ^{[1
]}

Gavard, O ^{[1
]}

Alais, J ^{[1
]}

Bonnaffé, D ^{[1
]}

机构：

[1] Univ Paris Sud, Inst Chim Mol Orsay, CNRS, Lab Chim Organ Multifonctionnelle, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 03期

关键词：

L-idose; L-iduronic acid; glycosaminoglycans; heparin; organometallic; oxidation;

D O I：

10.1016/S0040-4039(99)02080-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(PhS)(3)CLi adds with a total L-ido selectivity onto 3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-dialdose 2, opening the way to the most efficient preparation of 1,2,4-tri-O-acetyl-3-O-benzyl-L-iduronyl synthon 8. Alternatively, in view of combinatorial syntheses, aldehyde 2 allows a good access to vinylic L-ido and D-gluco synthons which may be converted into uronic acid by a sequence involving a new aldehyde oxidation by m-CPBA in aqueous solution. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：307 / 311

页数：5

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