Journal
CARBOHYDRATE RESEARCH
Volume 369, Issue -, Pages 42-47Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2013.01.004
Keywords
Chemical O-glycosylation; Photoredox catalysis; Visible light photocatalysis; Selenoglycosides
Funding
- Louisiana State University
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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 alpha-anomers with selectivities that vary with solvent. This represents the first example of a visible light-promoted O-glycosylation. (C) 2013 Elsevier Ltd. All rights reserved.
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