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Updated: Aug 9, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
Beta-selective glycosylations with masked D-mycosamine precursors
1Department of Chemistry, University of California, Irvine, California, 92697-2025, USA.
Abstract:
[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.
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