Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis

被引：54

作者：

Postema, MHD ^{[1
]}

Calimente, D ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 26期

关键词：

glycal; metathesis; ester; C-disaccharide;

D O I：

10.1016/S0040-4039(99)00815-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enitol (5a) with a variety of sugar based carboxylic acids 6a-d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d and exposure to the Schrock molybdenum catalyst 1 in warm toluene, in the box, gave the target C-disaccharide glycals 9a-d in good yield. The 1,6-linked gluco based C-disaccharide glycal 9a was converted to the 2-deoxy-beta-gluco-derivative 10a and the corresponding and gluco beta-gluco-C-disaccharide 13. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4755 / 4759

页数：5

共 46 条

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