Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors
© 2018 American Chemical Society. 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.
Publication Source (Journal or Book title)
Lacey, K., Quarels, R., Du, S., Fulton, A., Reid, N., Firesheets, A., & Ragains, J. (2018). Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors. Organic Letters, 20 (17), 5181-5185. https://doi.org/10.1021/acs.orglett.8b02125