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Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors
Kristina D Lacey1, Rashanique D Quarels1, Shaofu Du1
1Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.
Abstract:
Two classes of thioglycoside, 4-(4-methoxyphenyl)-3-butenylthioglycosides (MBTGs) and 4-(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), undergo acid-catalyzed O-glycosylations with a range of sugar and nonsugar alcohols at 25 °C. Electron density at the styrene alkene is critical for reactivity while sugar protecting group patterns have a minimal effect. In contrast with most methods for thioglycoside activation, acid-catalyzed activation of MBTGs is compatible with electroneutral alkenes.
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