Journal
ORGANIC LETTERS
Volume 10, Issue 19, Pages 4203-4206Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801316f
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Funding
- the National Science Foundation [518283]
- the American Heart Association [043285N]
- Louisiana Board of Regents
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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.
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