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N- and C-acyclic thionuleoside analogues of 1,2,3-triazole

✍ Scribed by Najim A. Al-Masoudi; Yaseen A. Al-Soud; Asmehan Abdul-Zahra

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
141 KB
Volume
15
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Cycloaddition of the azide derivative 5 with 1,4‐dihydroxybutyne afforded the N‐thio‐acyclic nucleoside 6, which prepared alternatively from coupling of the bromo derivative 8 with 2‐acetoxy‐ethylmercaptan. Deblocking of 6 gave the free nucleoside 7. Mesylation of 6 furnished the dimesylate 9, which gave three rearranged products 14–16 on treatment with chloride anion. These compounds might be obtained via the episulfonium ion 10, which is subjected to nucleophilic displacement and further sulfur participation. Deblocking of 14–16 afforded the free nucleoside analogues 17–19, and their structures were confirmed by COSY, ROESY, HMQC, and HMBC NMR techniques. Compound 16 was prepared alternatively from chlorination of alcohol 6 with Ph~3~P‐CCl~4~. Carbomoylation of 6 led to the carbamate 20, which gave the free nucleoside analogue 21 on deblocking. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:380–387, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20030

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