Some 2′-Modified 4′-Thionucleosides via Sulfur Participation and Synthesis of Thio-Azt from 4′-Thiofuranoid 1, 2-Glycal

NA Al-Masoudi, YA Al-Soud…

Index: Al-Masoudi, Najim A.; Al-Soud, Yaseen A.; Khodair, Ahmed I. Phosphorus, Sulfur and Silicon and the Related Elements, 2003 , vol. 178, # 6 p. 1199 - 1209

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Citation Number: 3

Abstract

ThioAZT 14 was synthesized in eight steps from D-arabinose derivative 4 via the new thiofuranoid 1, 2-glycal, 5-O-Acetyl-1, 2, 4-trideoxy-1, 4-epithio-3-Op-toluenesulfonyl-D-threo- pent-1-enitol (8). Ribosylation of the thiosugar 6 with thymine afforded regioselectively the nucleoside 16. Treatment of 16 with sodium azide in hot DMF gave, after spontaneous intramolecular displacment, the 2'-azido-xylo derivative 18, which furnished the free ...