Regioselective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions.
We have carried out a series of esterification reactions of secondary alcohols derived from d-glucose, d-mannose, and d-galactose via the Mitsunobu reaction. The benzoylation reaction of vicinal diols derived from monosaccharides under Mitsunobu conditions afforded monobenzoates with retention of stereochemistry only. The regioselectivity of these reactions depends on the stereochemistry of the sugar starting material. The Mitsunobu reactions on these diols may be used for the selective protection of other vicinal secondary hydroxyl groups.
Wang
Guijun
G
Department of Chemistry, Univeristy of New Orleans, New Orleans, Louisiana 70148, USA. gwang2@uno.edu
Ella-Menye
Jean-Rene
JR
St Martin
Michael
M
Yang
Hao
H
Williams
Kristopher
K