Deshpande, Sachin G. ; Suresh, Cheravakkattu G. ; Pathak, Tanmaya (2008) Studies on the synthesis and unusual behavior of vinyl sulfone-modified hexenopyranosylthymines Carbohydrate Research, 343 (7). pp. 1163-1170. ISSN 0008-6215
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.carres.2008.02.016
Abstract
Although vinyl sulfone-modified- (VSM) pent-2'-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycoside 4 are easily synthesized from the corresponding mesylated sulfones 1c and 3c, respectively, via an oxidation–mesylation–elimination route, the 3'-C-sulfonyl-hex-2'-enopyranosylthymine 11 is not obtained from 10 and a glycal derivative 12 is formed instead. On the other hand, 3'-C-sulfonyl-hex-3'-enopyranosylthymine 20 is easily synthesized from the mesylated sulfone 19. Again unlike the reaction patterns of VSM-pent-2'-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycosides 4 as Michael acceptors, the reactions of nucleophiles with 3'-C-sulfonyl-hex-3'-enopyranosylthymine 20 yielded a rearranged product 21 instead of Michael adducts.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Hexopyranosyl Nucleosides; Vinyl Sulfone-modified Nucleosides; Unsaturated Nucleosides; Michael Addition; Glycal |
| ID Code: | 104120 |
| Deposited On: | 17 Mar 2017 09:39 |
| Last Modified: | 17 Mar 2017 09:39 |
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