Beta-selective glycosylations with masked D-mycosamine precursors.
[reaction: see text]. 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 reactions. The alpha-bromo ketone 19 was synthesized from protected mycosamine and employed in an intermolecular S(N)2 glycosylation reaction. Both routes were successful for the model alcohol, cholesterol.
Packard
G K
GK
Department of Chemistry, University of California, Irvine, California, 92697-2025, USA.
Rychnovsky
S D
SD
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D002784:Cholesterol / Q000737:chemistry; D006031:Glycosylation; D006595:Hexosamines / Q000737:chemistry*; D018942:Macrolides
D000900:Anti-Bacterial Agents; D006595:Hexosamines; D018942:Macrolides; C014692:mycosamine; D002784:Cholesterol