An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides

Mark Spell; Xiaoping Wang; Amir E Wahba; Elizabeth Conner; Justin Ragains

doi:10.1016/j.carres.2013.01.004

An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides

Carbohydr Res. 2013 Mar 22:369:42-7. doi: 10.1016/j.carres.2013.01.004. Epub 2013 Jan 16.

Authors

Mark Spell¹, Xiaoping Wang, Amir E Wahba, Elizabeth Conner, Justin Ragains

Affiliation

¹ Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA 70803, United States.

PMID: 23399745
DOI: 10.1016/j.carres.2013.01.004

Abstract

Exceptionally mild procedures for the visible light photocatalytic activation of selenoglycoside donors in the presence of alcohol acceptors have been developed. This process is demonstrated with both 1-phenylselenyl-2,3,4,6-tetra-O-benzyl glucoside (1) and 1-phenylselenyl-2,3,4,6-tetra-O-benzyl galactoside (2). Catalysis is effected with both metal (Ru(bpy)3) and organocatalysts (diphenyldiselenide). Reactions afford, in all cases, primarily the α-anomers with selectivities that vary with solvent. This represents the first example of a visible light-promoted O-glycosylation.

Publication types

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

MeSH terms

Alcohols / chemistry*
Glycosides / chemistry*
Glycosylation
Light*
Photochemistry / methods*

Substances

Alcohols
Glycosides