Stereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-L-allitol using a D-mannose-derived cyclic nitrone

TitleStereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-L-allitol using a D-mannose-derived cyclic nitrone
Publication TypeJournal Article
Year of Publication2009
AuthorsBande, OP, Jadhav, VH, Puranik, VG, Dhavale, DD, Lombardo, M
JournalTetrahedron Letters
Volume50
Issue49
Pagination6906-6908
Date PublishedDEC
ISSN0040-4039
KeywordsCyclic nitrone, Enzyme inhibitors, Iminosugars, pyrrolidine
Abstract

Intramolecular N-alkylation of 2,3-O-isopropylidene-5-O-methanesulfonyl-6-O-t-butyldimethylsilyl-D-mann ofuranose-oxime 7 afforded a five-membered cyclic nitrone 9, which on N-O bond reductive cleavage followed by deprotection of -OTBS and acetonide functionalities gave 1,4-dideoxy-1,4-imino-L-allitol (DIA) 3. Addition of allylmagnesium chloride to nitrone 9 afforded alpha-allylated product 10a in high diastereoselectivity providing an easy entry to N-hydroxy-C1-alpha-allyl-substituted pyrrolidine iminosugar 4a after removal of protecting group, while N-O bond reductive cleavage in 10a afforded C1-alpha-allyl-pyrrolidine iminosugar 4b. (C) 2009 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2009.09.139
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.618

Divison category: 
Center for Material Characterization (CMC)