jo062640b_si_001.pdf (774.11 kB)
Synthesis of Deoxy Sugar Esters: A Chemoenzymatic Stereoselective Approach Affording Deoxy Sugar Derivatives Also in the Form of Aldehyde
journal contribution
posted on 2007-07-20, 00:00 authored by Ly Villo, Kady Danilas, Andrus Metsala, Malle Kreen, Imre Vallikivi, Sirje Vija, Tõnis Pehk, Luciano Saso, Omar ParveA 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.