Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

8-1990

Journal or Book Title

The Journal of Organic Chemistry

Volume

55

Issue

16

First Page

4922

Last Page

4925

DOI

10.1021/jo00303a031

Abstract

A new synthesis of mono C-glycosyl derivatives of dialdehyde sugars using a Michael additionlaldol 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.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 55(16); 4922-4925. Doi: 10.1021/jo00303a031. Copyright 1990 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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