Das, Indrajit ; Suresh, Cheravakkattu G. ; Decout, Jean-Luc ; Pathak, Tanmaya (2008) Unusual addition of amines to C-2 of vinyl sulfone-modified-β-D-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides Carbohydrate Research, 343 (8). pp. 1287-1296. 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.2008.03.022
Abstract
When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the β-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the-D -arabino configuration. Selected products were desulfonylated to obtain a new class of β-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Vinyl Sulfone-modified Carbohydrates; Amino Sugars; Deoxyaminosugars; Diastereoselective Michael addition; Desulfonylation with Mg–MeOH–NiBr2 |
| ID Code: | 104107 |
| Deposited On: | 17 Mar 2017 09:39 |
| Last Modified: | 17 Mar 2017 09:39 |
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