SYNTHESIS OF METHYL-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE, Y-4-C-METHYL-BETA-D-GLYCERO-PENTOFURANOSYL)THYMINE AND METHYL-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)THYMINE
H. Hrebabecky et A. Holy, SYNTHESIS OF METHYL-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE, Y-4-C-METHYL-BETA-D-GLYCERO-PENTOFURANOSYL)THYMINE AND METHYL-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)THYMINE, Collection of Czechoslovak Chemical Communications, 58(7), 1993, pp. 1668-1674
Reaction of isopropylidene derivative I with thionyl chloride in hexam
ethylphosphoric triamide afforded chloro derivative II. Removal of the
isopropylidene group in II by treatment with a cation-exchanging resi
n (H+ form) gave the free chloro nucleoside III. Reduction of the chlo
ro derivative II with tributylstannane and subsequent removal of the i
sopropylidene group yielded deoxy derivative V. This was protected wit
h tert-butyldiphenylsilyl group and converted into the mesylate VII. E
limination of the mesyl group followed by desilylation gave -methyl-be
ta-D-glycero-pent-2-enofuranosyl)thymine (IX) which was hydrogenated t
o afford y-4-C-methyl-beta-D-glycero-pentofuranosyl)thymine (X). methy
l-2-deoxy-beta-D-threo-pentofuranosyl)thymine (XIII) was prepared by m
esylation of isopropylidene derivative 1, nucleophilic substitution of
the mesyl group with azide and removal of the isopropylidene group.