METHYL 5-O-TERT-BUTYLDIPHENYLSILYL-2-DEOXY-D-THREO-PENTOFURANOSIDE; AN APPROACH TO THE SYNTHESIS OF 3'-SUBSTITUTED-2',3'-DIDEOXYNUCLEOSIDES INCLUDING 3'-AZIDO-3'-DEOXYTHYMIDINE AND OF 3'-SUBSTITUTED-2',3'-DIDEOXY-C-NUCLEOSIDES

Article abstract of DOI:10.1016/S0040-4039(00)95550-3

The Barton deoxygenation of methyl 3,5-O-isopropylidene-αβ-D-xylofuranoside is the key step in a short synthesis of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-αβ-D-threo-pentofuranoside (1) from D-xylose.The syntheses of methyl 2,3-dideoxy-3-fluoro-αβ-D-erythro-pentofuranoside and of a protected 3-azido-2,3-dideoxy-D-erythro-pentofuranose, a possible intermediate for the synthesis of 3'-azido-3'-deoxythymidine (AZT), are reported and the potential of (1) as a divergent intermediate for the preparation of 3'-substituted-2',3'-dideoxynucleosides and C-nucleoside analogues is discussed.