Lipase Catalyzed Diastereoselective Deacetylations of Anomeric Mixtures of Peracetylated 2′-Deoxynucleosides

Abstract

Lipase catalyzed deacetylations of anomeric mixtures of peracetylated 2′-deoxyribofuranosyl- and 2′-deoxyribopyranosyl thymine nucleosides 1 and 5 have been investigated. Generally, the diastereoselectivity was more pronounced in pure phosphate buffer than in phosphate buffer containing 10% DMF. Wheat Germ Lipase and Porcine Liver Esterase catalyzed diastereoselective deacetylation of 1 affording the pure β-anomer thymidine (4β) as the only completely deprotected nucleoside product.