Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides

ESTEBAN D. GUDI Ñ O, ADOLFO M. IRIBARREN, LUIS E. IGLESIAS

BIOCATALYSIS AND BIOTRANSFORMATION

TAYLOR & FRANCIS LTD

Año: 2010 vol. 28 p. 267 - 271

1024-2422

Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl a , b -D-ribofuranosides was assayed. Methyl and ethyl 2,3-di- O -acetyl- a , b -D-ribofuranosides enriched in the a -anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri- O -acetyl- b -D-ribofuranoside gave the new isopropyl 2,3-di- O -acetyl- b -D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl a , b -D-ribofuranosides reacted without selectivity.