Sanki, Aditya K. ; Suresh, Cheravakkattu G. ; Falgune, Usha D. ; Pathak, Tanmaya (2003) Anomeric configuration-directed diastereoselective C-C bond formation in vinyl sulfone-modified carbohydrates: a general route to branched-chain sugars Organic Letters, 5 (8). pp. 1285-1288. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol0342047
Related URL: http://dx.doi.org/10.1021/ol0342047
Abstract
This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy group. This novel concept of anomeric configuration-directed stereocontrolled carbon-carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched-chain sugars and densely functionalized carbohydrates.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 104200 |
| Deposited On: | 17 Mar 2017 09:06 |
| Last Modified: | 17 Mar 2017 09:07 |
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