31 research outputs found
SYNTHESIS OF DEOXY SUGAR ESTERS: A CHEMOENZYMATIC STEREOSELECTIVE APPROACH AFFORDING DEOXY SUGAR DERIVATIVES ALSO IN THE FORM OF ALDEHYDE.
A chemoenzymatic synthesis of deoxy sugar esters is described. The synthesis is
based on the O-alkylation of carboxylic acid with 2-bromo-5-acetoxypentanal. The
method allows treatment of hydroxy carboxylic acids without protection of
alcoholic hydroxyl groups. Several stereoisomeric deoxy sugar esters were
resolved (up to ee or de > 98%) using a lipase-catalyzed acetylation of
hemiacetals that in certain cases afforded deoxy sugar derivatives in the form of
aldehydes. The stereochemistry of the reactions was determined by the NMR spectra
of mandelic acid derivatives