PRACTICAL SYNTHESIS OF BETA-D-XYL-(1-]2)-BETA-D-MAN-(1-]4)-ALPHA-D-GLC-OME, A TRISACCHARIDE COMPONENT OF THE HYRIOPSIS-SCHLEGELII GLYCOSPHINGOLIPID

被引：49

作者：

LICHTENTHALER, FW

SCHNEIDERADAMS, T

IMMEL, S

机构：

[1] Institut für Organische Chemie, Technische Hochschule Darmstadt, D-64287 Darmstadt

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 22期

关键词：

D O I：

10.1021/jo00101a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By employing the readily accessible (preceding paper in this issue) 3,4,6-tri-O-benzyl-alpha-D-arabino-hexosyl bromide (1) as an indirect, beta-specific mannosyl donor, a practical three-step synthesis was elaborated for methyl xylosyl-beta(1-->2)-mannosyl-beta(1-->4)-glucoside (11), a trisaccharide component of Hyriopsis schlegelii ceramide oligosaccharides. Key steps were the silver aluminosilicate-induced, beta-specific glycosidation of 1 with methyl 2,3,6-tri-O-benzyl-alpha-D-glucoside and the silver triflate-promoted beta-xylosylation with 2,3,4-tri-O-benzoyl-alpha-D-xylosyl bromide. The overall yield amounted to a satisfactory 47%.

引用

页码：6735 / 6738

页数：4

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[1] MOLECULAR GRAPHICS - HOW TO SEE A MOLECULAR SCENARIO WITH THE EYES OF A MOLECULE [J].