133908-22-2Relevant articles and documents
Synthetic Approaches to 3'-Azido-3'-deoxythymidine and Other Modified Nucleosides
Jung, Michael E.,Gardiner, John M.
, p. 2614 - 2615 (1991)
An efficient stereospecific total synthesis of AZT (nine steps from crotonaldehyde) is reported in which the chirality is introduced via Sharpless epoxidation and therefore intermediates for the synthesis of both D- and L-AZT are easily produced.
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
Fleet, George W. J.,Son, Jong Chan
, p. 3615 - 3618 (2007/10/02)
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.