Stereodirected synthesis of aryl alpha-C-glycosides from 2-O-arylsilyl-glucopyranosides.
[reaction: see text] An efficient procedure for the stereoselective synthesis of aryl alpha-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.
D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism
D001593:Benzyl Compounds; D006027:Glycosides; D017646:Organosilicon Compounds; D011714:Pyrans