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  • Title: Asymmetric dihydroxylation of d-glucose derived alpha,beta-unsaturated ester: synthesis of azepane and nojirimycin analogues.
    Author: Dhavale DD, Markad SD, Karanjule NS, PrakashaReddy J.
    Journal: J Org Chem; 2004 Jul 09; 69(14):4760-6. PubMed ID: 15230599.
    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.
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