Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation-Michael addition reaction.
2,2-Bis(C-branched-chain)glucopyranosid-3-uloses, designed for the preparation of biologically active natural product iridoid derivatives, are synthesized selectively by the new reaction of butenolide-containing sugar with active methylene compounds, and the new reaction is clarified as autoxidation followed by Michael addition of carbanion.
Liu
Hong-Min
HM
Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, PR China. liuhm@zzu.edu.cn
Zhang
Fuyi
F
Zou
Da-Peng
DP
D002264:Carboxylic Acids / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry*; D007661:Ketoses / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013997:Time Factors
D002264:Carboxylic Acids; D006027:Glycosides; D006601:Hexoses; D007661:Ketoses