Synthesis of 3′,5′-dithiothymidine and related compounds
Journal of the Chemical Society - Perkin Transactions 1, ISSN: 0300-922X, Issue: 18, Page: 2237-2240
1996
- 18Citations
- 9Captures
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Article Description
When 3′,5′-di-O-mesylthymidine 7 is heated first with Methylamine in ethanol solution and then with the sodium salt of 4-methoxyphenylmethanethiol 9 in N,N-dimethylacetamide (DMA) solution, the bis(sulfide) 11a is obtained in high yield; when the dimesyl ester 7 is treated with the same thiolate salt in hexamethylphosphoric triamide (HMPA) solution at room temperature, the threo-bis(sulfide) 12a is obtained stereospecifically. Treatment of the two bis(sulfides) 11a and 12a first with 2-nitrobenzenesulfenyl chloride 10 in acetic acid-dichloromethane (1:9 v/v) at 0°C and then with zinc in hot acetic acid gives 3′,5′-dithiothymidine 5a and the cyclic disulfide 16, respectively, as crystalline solids in good overall yields. Although attempts to isolate the pure threo-dithio compound 12b lead to the formation of the cyclic disulfide 16, when the crude material is treated with 2,2-dimethoxypropane in the presence of acid, its 3′,5′-S-isopropylidene derivative 17 is obtained and isolated as a crystalline solid in good overall yield.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=33749143183&origin=inward; http://dx.doi.org/10.1039/p19960002237; https://xlink.rsc.org/?DOI=P19960002237; http://xlink.rsc.org/?DOI=P19960002237; http://pubs.rsc.org/en/content/articlepdf/1996/P1/P19960002237; https://dx.doi.org/10.1039/p19960002237; https://pubs.rsc.org/en/content/articlelanding/1996/p1/p19960002237
Royal Society of Chemistry (RSC)
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