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

TitleSynthesis of azepane and nojirimycin iminosugars: the sharpless asymmetric epoxidation of D-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide
Publication TypeJournal Article
Year of Publication2010
AuthorsJadhav, VH, Bande, OP, Puranik, VG, Dhavale, DD
JournalTetrahedron-Asymmetry
Volume21
Issue2
Pagination163-170
Date PublishedFEB
ISSN0957-4166
Abstract

The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-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 dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetasy.2010.01.007
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.484

Divison category: 
Center for Material Characterization (CMC)