Asymmetric dihydroxylation of d-glucose derived alpha,beta-unsaturated ester: synthesis of azepane and nojirimycin analogues |
| |
Authors: | Dhavale Dilip D Markad Shankar D Karanjule Narayan S PrakashaReddy J |
| |
Institution: | Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India. ddd@chem.unipune.ernet.in |
| |
Abstract: | The asymmetric dihydroxylation of a d-glucose derived alpha,beta-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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|