A NEW SYNTHESIS OF ARYL MONO C-GLYCOSYL DERIVATIVES OF DIALDEHYDE SUGARS

被引：23

作者：

KRAUS, GA

SHI, J

机构：

[1] Department of Chemistry, Iowa State University, Ames

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 16期

关键词：

D O I：

10.1021/jo00303a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of mono C-glycosyl derivatives of dialdehyde sugars using a Michael addition/aldol condensation sequence has been developed. It is complementary to previously reported methods for the production of C-glycosyl compounds. The synthesis involves the Michael addition reaction of an enol silyl ether with acetylbenzoquinone followed by an aldol condensation and subsequent aromatization of the resulting hydroxy ketone. The aldol condensation proceeds only under select conditions and affords the unstable ketols 7 and 15. © 1990, American Chemical Society. All rights reserved.

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页码：4922 / 4925

页数：4

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