Approximate H(5) Ring Conformation of 2,3-O-Carbonate Protected α- and β-L-Rhamnopyranosides as Confirmed by X-Ray Crystallography.

Authors:
David Crich
David Crich
Wayne State University
United States
Donald J Wink
Donald J Wink
University of Illinois at Chicago
United States

ARKIVOC 2005 Aug;2005(6):339-344

2,3-O-Carbonate protected rhamnopyranosides with both the α- and β-anomeric configuration are shown crystallographically to have ring conformations that differ significantly from the chair and which approach the (o)H(5) half-chair. This distortion, which is greatest in the α-anomer, provides a basis for the α-selectivity of 2,3-O carbonate protected manno- and rhamnopyranosyl donors as well as the conformationally related 2,3-O-alkylidene derivatives, in homogeneous solution phase glycosylation reactions.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2386999PMC
August 2005
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