Pseudouridine transformations. Formation of 2′- and 3′-deoxypseudouridines via halogen intermediates using α-acetoxyisobutyryl chloride

Abstract

Treatment of pseudouridine (1) with α-acetoxyisobutyryl chloride (neat or in acetonitrile solution) at elevated temperatures followed by hydrogenolysis of the resulting mixture of chloro-sugar intermediates and deblocking gave the 2′- and 3′-deoxypseudouridines (2) and (3)(ca. 90%) in a ratio of ca. 55:45 with no evidence for the previously suggested α-anomer (4) of 2′-deoxypseudouridine.