Synthesis of eight-membered iminocyclitols from D-glucose

TitleSynthesis of eight-membered iminocyclitols from D-glucose
Publication TypeJournal Article
Year of Publication2010
AuthorsJadhav, VH, Bande, OP, Puranik, VG, Dhavale, DD
JournalTetrahedron
Volume66
Issue15
Pagination2830-2834
Date PublishedAPR0
ISSN0040-4020
KeywordsBaylis-Hillman reaction, Conjugate addition, diastereoselectivity, Iminosugars
Abstract

The Baylis-Hillman reaction of 3-o-benzyl-alpha-d-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated alpha-methylene-beta-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2010.02.044
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.011

Divison category: 
Center for Material Characterization (CMC)