Chakraborty, Chaitali ; Dhavale, Dilip D. (2006) Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the henry reaction Carbohydrate Research, 341 (7). pp. 912-917. ISSN 0008-6215
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00086...
Related URL: http://dx.doi.org/10.1016/j.carres.2006.02.007
Abstract
The Henry reaction with the easily available α-D-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the α-D-gluco- and β-l-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the α-D-gluco-nitroaldose as the only product. The reduction of the nitro group in the α-D-gluco- and β-L-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Carbohydrates; Henry Reaction; Enzyme Inhibitors; Azepanes |
ID Code: | 9736 |
Deposited On: | 02 Nov 2010 10:45 |
Last Modified: | 31 May 2011 11:53 |
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