Preparation of alpha-C-glycosides from glycals

J D Parrish; R Daniel Little

doi:10.1021/ol025575a

Preparation of alpha-C-glycosides from glycals

Org Lett. 2002 May 2;4(9):1439-42. doi: 10.1021/ol025575a.

Authors

J D Parrish¹, R Daniel Little

Affiliation

¹ Department of Chemistry & Biochemistry, University of California, Santa Barbara, Santa Barbara, California 93106, USA.

PMID: 11975598
DOI: 10.1021/ol025575a

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Calcium Gluconate / analogs & derivatives*
Calcium Gluconate / chemistry
Glycosides / chemical synthesis*
Indicators and Reagents
Oxidation-Reduction

Substances

Glycosides
Indicators and Reagents
Calcium Gluconate