Collect. Czech. Chem. Commun. 1993, 58, 1668-1674

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-threo-pentofuranosyl)thymine

Hubert Hřebabecký and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Reaction of isopropylidene derivative I with thionyl chloride in hexamethylphosphoric triamide afforded chloro derivative 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-(1-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine (XIII) was prepared by mesylation of the isopropylidene derivative I, nucleophilic substitution of the mesyl group with azide and removal of the isopropylidene group.