A versatile, three-component-reaction route to N-glycosylamines.
[figure: see text] Under the agency of N-bromosuccinimide, n-pentenyl glycosides, acetonitrile, and carboxylic acids participate in three-component-reactions that afford N-acylated glycosylamines. The procedure tolerate diverse donors, and C2-tetrachlorophthalimido and C2-azido groups effectively control anomeric stereoselectivity. Success of the procedure does not appear to depend on the acid's strength, but for an aromatic acid, substitution pattern affects the rate, while the presence of a lone pair on the para substituent inhibits the process.
Nair
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Natural Products and Glycotechnology Research Institute, Inc., 4118 Swarthmore Road, Durham, North Carolina 27707, USA.
Fraser-Reid
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B
Szardenings
A K
AK
D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000138:chemical synthesis; D006031:Glycosylation; D013237:Stereoisomerism
D006023:Glycoproteins; D005944:Glucosamine