A chemoenzymatic synthesis of deoxy sugar esters isdescribed. The synthesis is based on the O-alkylation ofcarboxylic acid with 2-bromo-5-acetoxypentanal. The methodallows treatment of hydroxy carboxylic acids without protection of alcoholic hydroxyl groups. Several stereoisomericdeoxy sugar esters were resolved (up to ee or de > 98%)using a lipase-catalyzed acetylation of hemiacetals that incertain cases afforded deoxy sugar derivatives in the formof aldehydes. The stereochemistry of the reactions wasdetermined by the NMR spectra of mandelic acid derivatives.
