Bicyclic diazasugars. Part 3: beta-D-mannose and 6-deoxy-beta-L-gulose analogues

Authors
Berges, DA Fan, JM Liu, NN Dalley, NK
Citation
Da. Berges et al., Bicyclic diazasugars. Part 3: beta-D-mannose and 6-deoxy-beta-L-gulose analogues, TETRAHEDRON, 57(50), 2001, pp. 9915-9924
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
50
Year of publication
2001
Pages
9915 - 9924
Database
ISI
SICI code
0040-4020(200112)57:50<9915:BDP3BA>2.0.ZU;2-I
Abstract
A bicyclic analogue of beta -D-mannopyranose with nitrogen atoms replacing the ring and glycosidic oxygen atoms has been prepared in a single step fro m 5-O-mesyl-D-mannofuranose by a process that likely involves double displa cement and an epoxide intermediate. A similar but protected bicyclic analog ue of 6-deoxy-beta -L-gulopyranose has been prepared by an electrophilic cy clization reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.