Preparation of alpha-C-glycosides from glycals.
[reaction: see text]. A novel approach to simple C-glycosides is reported. Reductive ring opening of 1,2-anhydro sugars with titanocene(III) chloride produces an anomeric radical that can be trapped with a variety of agents. The reaction stereospecifically affords alpha-glycosides and produces a free C-2 hydroxyl group allowing for further elaboration.
Parrish
J D
JD
Department of Chemistry & Biochemistry, University of California, Santa Barbara, Santa Barbara, California 93106, USA.
Little
R Daniel
RD
D002125:Calcium Gluconate / Q000031:analogs & derivatives* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010084:Oxidation-Reduction
D006027:Glycosides; D007202:Indicators and Reagents; D002125:Calcium Gluconate