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

Nicolas Blanchard; William R Roush

doi:10.1021/ol027257h

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

Org Lett. 2003 Jan 9;5(1):81-4. doi: 10.1021/ol027257h.

Authors

Nicolas Blanchard¹, William R Roush

Affiliation

¹ Department of Chemistry, University of Michigan, 930 North University, Ann Arbor, MI 48109-1055, USA.

PMID: 12509896
DOI: 10.1021/ol027257h

Abstract

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]

Publication types

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

MeSH terms

Fluorides / chemistry*
Glycosides / chemical synthesis*
Glycosides / chemistry*
Ketones / chemistry*
Molecular Structure
Stereoisomerism

Substances

Glycosides
Ketones
Fluorides

Grants and funding

GM 38436/GM/NIGMS NIH HHS/United States