Selective monodeacetylation of methyl 2,3,5-tri-O-acetyl-D-arabinofuranoside using biocatalyst

Abstract

Methyl arabinofuranoside 1 was fully acetylated to methyl 2,3,5-tri-O-acetyl-D-arabinofuranoside 2 and it was regio-selectively deacetylated using enzymes. Rhizopus oryzae esterase gave methyl 3,5-di-O-acetyl-D-arabinofuranoside 3, regioselectively. This protected 3 was deoxygenized to 3,5-di-O-acetyl-D-2-deoxyarabinofuranoside 7 using hypophosphorous acid. (c) 2005 Elsevier Ltd. All rights reserved.