SYNTHESIS OF 1-(2,3-DIDEOXY-4-C-METHYL-&β-D-glycero-PENT-2-ENOFURANOSYL)THYMINE, 1-(2,3-DIDEOXY-4-C-METHYL-&β-D-glycero-PENTOFURANOSYL)THYMINE AND 1-(4-C-AZIDOMETHYL-2-DEOXY-&β-D-threoPENTOFURANOSYL)THYMINE

Article abstract of DOI:10.1135/cccc19931668

Reaction of isopropylidene derivative I with thionyl chloride in hexamethylphosphoric triamide afforded chloroderivative II.Removal of the isopropylidene group in II by treatment with a cation-exchanging resin (H⁺ form) gave the free chloro nucleoside III.Reduction of the chloro derivative II with tributylstannane and subsequent removal of the isopropylidene group yielded deoxy derivative V.This was protected with tert-butyldiphenylsilyl group and converted into the mesylate VII.Elimination of the mesyl group followed by desilylation gave 1-(2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine (IX) which was hydrogenated to afford 1-(2,3-dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine (X). 1-(4-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine (XIII) was prepared by mesylation of isopropylidene derivative I, nucleophilic substitution of the mesyl group with azide and removal of the isopropylidene group.