SYNTHESIS OF ALPHA-METHYL 1',2'-DIDEOXYCELLOBIOSIDE - A NOVEL C-DISACCHARIDE

被引：38

作者：

ARMSTRONG, RW

TEEGARDEN, BR

机构：

[1] Department of Chemistry and Biochemistry, University of California, Los Angeles

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 03期

关键词：

D O I：

10.1021/jo00029a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bromonium ion induced 6-endo-trig cyclizations of E olefine derived from D-arabinose provide a stereoselective route to 2'-deoxyglucono-beta-C-glycosides. Use of delta-alkenols containing allylic isopropylidenes (i.e., 1) prevents formation of furan products due to the highly strained transition state necessary for formation of the trans [3.3.0] bicyclic systems. Because the exo-anomeric carbon is not involved in the cyclization, previously established stereocenters at this carbon are left intact. Application of this methodology to the synthesis of alpha-methyl 1',2'-dideoxycellobioside (22) is presented. The restricted rotation about the bond connecting the two sugars affords a unique staggared conformation of the disaccharide.

引用

页码：915 / 922

页数：8