Ravindran, Bindu ; Deshpande, Sachin G. ; Pathak, Tanmaya (2001) Vinylsulfone-modified carbohydrates: first general route to D-lividosamine (2-amino-2,3-dideoxy-D-glucose) and its new analogues Tetrahedron, 57 (6). pp. 1093-1098. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/S0040-4020(00)01081-4
Abstract
A general route to D-lividosamine and its new analogues has been devised for the first time. The essence of the present synthetic route lies in the diastereoselective introduction of N-monoalkylated and N-dialkylated amines to C-2 carbons of methyl 2,3-dideoxy-3-C-phenylsulfonyl-α-D-hex-2-enopyranoside and methyl 2,3-dideoxy-3-C-phenylsulfonyl-β-D-hex-2-enopyranoside in equatorial configurations. The 2-amino-2,3-dideoxysugrs thus generated, are desulfonated reductively at C-3 sites to produce a known intermediate for the synthesis of D-lividosamine and several new 2-N-alkylamino- and 2-N,N-dialkylamino-2,3-dideoxy analogues.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | D-lividosamine; Carbohydrates; Vinyl Sulfone; Michael Addition |
| ID Code: | 104206 |
| Deposited On: | 17 Mar 2017 07:34 |
| Last Modified: | 17 Mar 2017 07:34 |
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