Targeted glycosyl donor delivery for site-selective glycosylation.
[reaction: see text]n-Pentenyl ortho esters (NPOEs) and n-pentenyl glycosides (NPGs) are interconvertible glycosyl donors which are activated by reaction with halonium ions. In a series of cyclic syn-1,3-diols, NPOEs have been found to specifically glycosylate the equatorial-OH while the NPG glycosylates predominantly, but not exclusively, the axial-OH. When the cyclic diol acceptor is presented with equivalent amounts of an NPOE and an NPG in a three-component-reaction, a single, double-glycosylation product is obtained, which conforms to the foregoing preferences, presenting evidence for site-selective glycosylation.
Anilkumar
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G
Natural Products and Glycotechnology Research Institute, Inc., Durham, North Carolina 27707, USA.
Nair
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LG
Fraser-Reid
B
B
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data
D000475:Alkenes; D006027:Glycosides; D007202:Indicators and Reagents