Some 2′-modified 4′-thionucleosides via sulfur participation and synthesis of Thio-AZT from 4′-thiofuranoid 1,2-glycal

Article abstract of DOI:10.1080/10426500307902

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-O-p-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 nucleoside 19 on treatment with methanolic ammonia. Similarly, treatment of 16 with sodium ethylthiolate in boiling methanol led to inversion in configuration and gave, after several intramolecular displacments, via the sulfur participation, the 2′,3′-diethylthiolate-ribo derivative 23. Deblocking of 23 with methanolic ammonia afforded the free nuclaoside 24.