A new synthesis of aryl mono C-glycosyl derivatives of dialdehyde sugarsThe Journal of Organic Chemistry
Publication VersionPublished Version
AbstractA 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.
Copyright OwnerAmerican Chemical Society
Citation InformationGeorge 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/