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Synthesis of Deoxy Sugar Esters:  A Chemoenzymatic Stereoselective Approach Affording Deoxy Sugar Derivatives Also in the Form of Aldehyde

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journal contribution
posted on 20.07.2007 by Ly Villo, Kady Danilas, Andrus Metsala, Malle Kreen, Imre Vallikivi, Sirje Vija, Tõnis Pehk, Luciano Saso, Omar Parve
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.