2-Deoxy-2-iodo-beta-glucopyranosyl fluorides: mild and highly stereoselective glycosyl donors for the synthesis of 2-deoxy-beta-glycosides from beta-hydroxy ketones.
2-Deoxy-2-iodo-beta-glucopyranosyl fluoride 14 is a highly stereoselective glucopyranosyl donor that may be activated under mild conditions. Application of this new glycosyl donor to the glycosidation reactions of a variety of acceptors including beta-hydroxy ketones affords beta-glycosides with high efficiency and stereoselectivity. [reaction--see text]
Blanchard
Nicolas
N
Department of Chemistry, University of Michigan, 930 North University, Ann Arbor, MI 48109-1055, USA.
Roush
William R
WR
D005459:Fluorides / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006027:Glycosides; D007659:Ketones; D005459:Fluorides