Title
Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors
Document Type
Article
Publication Date
9-7-2018
Abstract
© 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)
Organic Letters
First Page
5181
Last Page
5185
Recommended Citation
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