FORMATION OF AN UNEXPECTED 2-DEOXY-ALPHA-D-THREO-PENTOFURANOSYL AZIDE BY REACTION OF O2, 3'-ANHYDRO-5'-O-TRITYL-2'-DEOXYCYTIDINE WITH LITHIUM AZIDE

Abstract

Reaction of O2,3'-anhydro-5'-O-trityl-2'-deoxycytidine (1) with LiN3 in DMF resulted in the formation of 1-(3-azido-2,3-dideoxy-5-O-trityl-beta-D-erythro-pentofuranosyl)cytosine (2) and 3-O-(4-amino-1,3-pyrimidin-2-yl)-5-O-trityl-2-deoxy-alpha-D-threo-pentof uranosyl azide (3) 2:3 = 1:1) in 88% yield. Compound 3 was deprotected with 80% aqueous AcOH yielding 4.