The synthesis of an O,C-trisaccharide:: The O,C-analog of methyl 4′-O-β-D-glucopyranosylgentiobioside

被引：21

作者：

Spak, SJ ^{[1
]}

Martin, OR ^{[1
]}

机构：

[1] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 02期

基金：

美国国家卫生研究院;

关键词：

nitroaldol; C-glycosides; cellobiosylnitromethane;

D O I：

10.1016/S0040-4020(99)00923-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of an O,C-trisaccharide, namely methyl O-beta-D-glucopyranosyl-(1-->4)-C-beta-D-glucop glucopyranoside, was achieved in 14 steps by way of the nitro-aldol coupling of hepta-O-acetyl-beta-cellobiosylnitromethane and methyl 6-aldehydo-2,3,4-tri-O-benzyl-alpha-D-gluco-1,5-pyranoside, followed by the elaboration of the coupling product. The resulting O,C-trisaccharide constitutes a potential inhibitor of the beta glucanases of the cellulase family. The perbenzylated derivative of cellobiosyl nitromethane was also prepared. Both disaccharide-C-glycosides constitute useful starting materials for the preparation of higher mixed O,C-oligosaccharides. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：217 / 224

页数：8

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