Bera, Sanjib ; Langley, Graham J. ; Pathak, Tanmaya (1998) Sugar-modified uridine bisvinyl sulfone: synthesis of a bifunctionalized nucleoside Michael acceptor and its use in stereoselective tandem cyclization The Journal of Organic Chemistry, 63 (6). pp. 1754-1760. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo9705576
Related URL: http://dx.doi.org/10.1021/jo9705576
Abstract
A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bond with biological nucleophiles. This compound could be used to generate a large number and a new class of bicyclic S,S-dioxidethiazine derivatives 8−12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13−15. The structures of compounds 8−12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 104268 |
| Deposited On: | 17 Mar 2017 06:20 |
| Last Modified: | 17 Mar 2017 06:20 |
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