beta-selective glycosylations with masked D-mycosamine precursors

Authors
Packard, GK Rychnovsky, SD
Citation
Gk. Packard et Sd. Rychnovsky, beta-selective glycosylations with masked D-mycosamine precursors, ORG LETT, 3(21), 2001, pp. 3393-3396
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
21
Year of publication
2001
Pages
3393 - 3396
Database
ISI
SICI code
1523-7060(20011018)3:21<3393:BGWMDP>2.0.ZU;2-F
Abstract
[GRAPHICS] Both an intramolecular aglycon delivery (IAD) method and an intermolecular S(N)2 displacement method were examined for beta -selective glycosylations of cholesterol with D-mycosamine. An anomeric sulfoxide, sulfide, selenide, and fluoride were all successfully used as glycosyl donors in IAD reaction s. The alpha -bromo ketone 19 was synthesized from protected mycosamine and employed in an intermolecular S(N)2 glycosylation reaction, Both routes we re successful for the model alcohol, cholesterol.