Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Organic Letters
Kristina D LaceyJustin R Ragains

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.

References

Mar 28, 2001·Science·C R Bertozzi, L L Kiessling
Mar 28, 2003·Organic Letters·Matteo AdinolfiMarialuisa Schiattarella
Aug 16, 2005·Chemical Society Reviews·Jeroen D C CodéeGijsbert A van der Marel
Aug 25, 2005·Journal of the American Chemical Society·Jin-Hwan KimGeert-Jan Boons
Apr 27, 2007·Nature·Peter H Seeberger, Daniel B Werz
Feb 18, 2010·Nature Chemistry·Thomas J BoltjeGeert-Jan Boons
Feb 8, 2011·Topics in Current Chemistry·Tze Chieh Shiao, René Roy
Jan 28, 2012·Journal of the American Chemical Society·Forest J Robertson, Jimmy Wu
Dec 22, 2012·Organic Letters·Walter J WeverAlbert A Bowers
Jul 3, 2013·Angewandte Chemie·Manibarsha GoswamiNicola L B Pohl
Mar 7, 2014·Organic Letters·An-Hsiang Adam ChuClay S Bennett
Apr 15, 2015·Accounts of Chemical Research·Peter H Seeberger
Feb 18, 2016·Organic & Biomolecular Chemistry·Hai Yu, Xi Chen
Apr 19, 2016·Angewandte Chemie·Mark L SpellJustin R Ragains

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Citations

Mar 21, 2020·Organic & Biomolecular Chemistry·Dancan K NjeriJustin R Ragains

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