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Article
A new synthesis of aryl mono C-glycosyl derivatives of dialdehyde sugars
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Jianmin Shi, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
8-1-1990
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
Citation Information
George A. Kraus and Jianmin Shi. "A new synthesis of aryl mono C-glycosyl derivatives of dialdehyde sugars" The Journal of Organic Chemistry Vol. 55 Iss. 16 (1990) p. 4922 - 4925
Available at: http://works.bepress.com/george_kraus/28/