Jadhav, Vrushali H. ; Bande, Omprakash P. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2010) Synthesis of azepane and nojirimycin iminosugars: the sharpless asymmetric epoxidation of D-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide Tetrahedron: Asymmetry, 21 (2). pp. 163-170. ISSN 0957-4166
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...
Related URL: http://dx.doi.org/10.1016/j.tetasy.2010.01.007
Abstract
The sharpless asymmetric epoxidation of D-glucose-derived allyl alcohol 4 afforded α- and β -epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido diol 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 9744 |
| Deposited On: | 02 Nov 2010 10:44 |
| Last Modified: | 31 May 2011 11:48 |
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