Tri-O-acyl 2-deoxy-D-ribofuranose: An effective enzyme-assisted one-pot synthesis from 2-deoxy-D-ribose and transformation into 2′-deoxynucleosides

Article abstract of DOI:10.1016/0040-4039(95)01216-5

Regioselective lipase-catalyzed (Novozym 435 from Candida antartica) acylations of unprotected 2-deoxy-D-ribose and D-ribose, by use of propionic anhydride, afforded the novel 5-0-monoacylated derivatives 1 and 4, respectively. Subsequent addition of acetic anhydride and pyridine into the reaction mixtures gave the corresponding per-0-acylated pentofuranoses 2 and 5 in almost quantitative overall yields from the unprotected carbohydrates. The versatility of compound 2 as an universal synthon for synthesis of anomeric mixtures of 2′-deoxynucleosides is demonstrated.