Synthesis of Homo-C-D4T and Homo-C-Thymidine.

Abstract s-C-Vinyl glycoside of D-arabinofuranose was converted to the β-C-hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2′,3′-dideoxy-2′,3′-didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.