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An alternative strategy for the synthesis of 3′-azido-2′,3′-dideoxy-4′-thionucleosides starting from d-xylose

✍ Scribed by Bougrine Tber; Nour-Eddine Fahmi; Gino Ronco; Pierre Villa; David F. Ewing; Grahame Mackenzie

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
832 KB
Volume
267
Category
Article
ISSN
0008-6215

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✦ Synopsis

Methyl 5- O-acetyl-3-azido-2,3-dideoxy-4-thio-a,fl-D-erythro-pentofuranoside and 1,5-O-diacetyl-3-azido-2,3-dideoxy-4-thio-a,[J-D-erythro-pentofuranose were prepared in twelve and thirteen steps, respectively, by an efficient route starting from D-xylose. Both compounds were easily converted into an anomeric mixture of pyrimidine nucleosides by reaction with the 2,4-bi(trimethylsilyloxy) derivative in the presence of a Lewis acid. The anomeric mixtures were separated by chromatography. The 4'-thio analogue of AZT and related uridine nucleosides have been prepared by a novel and more efficient approach.

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An improved synthesis of benzyl 3,5-di-O
An improved synthesis of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-d-erythro-pentofuranoside, an intermediate in the synthesis of 4′-thionucleosides
✍ Michael R. Dyson; Paul L. Coe; Richard T. Walker 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 846 KB

Treatment of methyl 3,5-di-O-benzyl-2-deoxy-a,8-r>-erythro-pentofuranoside with a-toluenethiol and cont. hydrochloric acid gave 3,5-di-0-benzyl-2-deoxy-D-erythro-pentose dibenzyl dithioacetal (21). Mesylation of 21 and ring closure gave benzyl 3,S-di-O-benzyl-2-deoxy-l,4-dithio-a,P-L-threo-pentofura