Dhavale, Dilip D. ; Markad, Shankar D. ; Karanjule, Narayan S. ; PrakashaReddy, J. (2004) Asymmetric dihydroxylation of D-glucose derived α, β-unsaturated ester: synthesis of azepane and nojirimycin analogues Journal of Organic Chemistry, 69 (14). pp. 4760-4766. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo049509t
Related URL: http://dx.doi.org/10.1021/jo049509t
Abstract
The asymmetric dihydroxylation of a D-glucose derived α,β-unsaturated ester 3 afforded syn vicinal diols in good to high diastereoselectivity. The conversion of these vicinal diols to the corresponding cyclic sulfate, regio-, stereoselective nucleophilic ring opening by sodium azide, and LAH reduction afforded amino heptitols 7a,b that were converted to azepane 1c,d and nojirimycin analogues 2c,d.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 75345 |
| Deposited On: | 22 Dec 2011 13:11 |
| Last Modified: | 22 Dec 2011 13:11 |
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