Bhattacharya, Rahul ; Pathak, Tanmaya (2009) Addition of amines and carbon nucleophiles to vinyl sulfone-modified 6-deoxy-hex-3-enopyranoside: a case of nucleophile dependent diastereoselectivity Carbohydrate Research, 344 (17). pp. 2336-2341. 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.2009.09.009
Abstract
Reactions of amines and carbon nucleophiles with 4-sulfonyl-hex-3-enopyranoside generate a range of C-3 amino- and C-3 branched-chain sugars, which are analogues of 3-amino-3,6-dideoxy sugars and 3-C-branched-chain-3,6-dideoxy sugars. The diastereoselectivity of addition reaction is nucleophile dependent; while both nitrogen and carbon nucleophiles added in cis-fashion, amines generated C3-C4 trans-diaxial products (gulo-derivatives), and carbon nucleophiles afforded C3–C4 trans-diequatorial products (gluco-analogues).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Vinyl Sulfone; Modified Carbohydrate; Michael Addition; Aminosugar; Branched-chain Sugar; Diastereoselectivity |
| ID Code: | 104071 |
| Deposited On: | 17 Mar 2017 10:42 |
| Last Modified: | 17 Mar 2017 10:42 |
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