Synthesis of 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl(thymine (d4T; stavudine) from 5-methyluridine

Article abstract of DOI:10.1080/07328319608002369

A practical synthetic method of d4T (3) from 5-methyluridine (2a) was developed. The Marumoto-Mansuri method was modified using 2',3'-O-methoxyethylidene-5-methyluridine (10) as an intermediate to afford 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine (6a) in high yield with less formation of byproducts. The reaction mechanism was also discussed.

Full text of DOI:10.1080/07328319608002369

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Synthesis of 1-(2,3-Dideoxy-β-d-
glycero-pent-2-enofuranosyl)thymine
(d4T; Stavudine) from 5-Methyluridine
Hiroshi Shiragami a , Takashi Ineyama a , Yumiko Uchida a &
Kunisuke Izawa a
a Central Research Laboratories, Ajinomoto Co., Inc. , 1-1
Suzuki-cho, Kawastaki-ku, Kawasaki, 210, Japan
Published online: 21 Aug 2006.
To cite this article: Hiroshi Shiragami , Takashi Ineyama , Yumiko Uchida & Kunisuke Izawa (1996)
Synthesis of 1-(2,3-Dideoxy-β-d-glycero-pent-2-enofuranosyl)thymine (d4T; Stavudine) from 5-
Methyluridine , Nucleosides and Nucleotides, 15:1-3, 47-58
To link to this article: http://dx.doi.org/10.1080/07328319608002369
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