Expedient stereospecific synthesis of beta-mannosides from a glucose-derived 1,2-orthoester

Authors
Kaji, E Hosokawa, Y
Citation
E. Kaji et Y. Hosokawa, Expedient stereospecific synthesis of beta-mannosides from a glucose-derived 1,2-orthoester, HETEROCYCLE, 52(2), 2000, pp. 579-582
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
2
Year of publication
2000
Pages
579 - 582
Database
ISI
SICI code
0385-5414(20000201)52:2<579:ESSOBF>2.0.ZU;2-L
Abstract
A new, stereospecific synthesis of beta-mannosides from glucose-derived 1,2 -orthoester has been developed using a simple four-step procedure. For the synthesis of beta-D-Man-(1-->6)-D-Gal, a 6-OH free galactose derivative was glycosylated with the orthoester to yield beta-D-Glc-(1-->6)-D-Gal; the Gl c unit of which was epimerized into the beta-mannoside in good yield.