Imino glycals in synthesis: Preparation of novel deoxymannojirimycin analogues

Authors
Desire, M Shipman, M
Citation
M. Desire et M. Shipman, Imino glycals in synthesis: Preparation of novel deoxymannojirimycin analogues, SYNLETT, (8), 2001, pp. 1332-1334
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
8
Year of publication
2001
Pages
1332 - 1334
Database
ISI
SICI code
0936-5214(200108):8<1332:IGISPO>2.0.ZU;2-R
Abstract
The synthesis of imino glucal 2 from tetra-O-benzyl-D-glucopyranose in 7 st eps is described. This imino sugar building block is converted into conform ationally constrained deoxymannojirimycin analogue (+)-9 by means of a ster eocontrolled cyclopropanation followed by a two step deprotection sequence. Regioselective fission of the cyclopropane ring prior to deprotection prov ides access to related analogue (+)-11.