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.
SYNTHESIS OF DEOXY SUGAR ESTERS: A CHEMOENZYMATIC STEREOSELECTIVE APPROACH AFFORDING DEOXY SUGAR DERIVATIVES ALSO IN THE FORM OF ALDEHYDE / Villo, L; Danilas, K; Metsala, A; Kreen, M; Vallikivi, I; Vija, S; Pehk, T; Saso, Luciano; Parve, O.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 72:(2007), pp. 5813-5816. [10.1021/jo062640b]
SYNTHESIS OF DEOXY SUGAR ESTERS: A CHEMOENZYMATIC STEREOSELECTIVE APPROACH AFFORDING DEOXY SUGAR DERIVATIVES ALSO IN THE FORM OF ALDEHYDE.
SASO, Luciano;
2007
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
