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. 2018 Sep 7;20(17):5181-5185.
doi: 10.1021/acs.orglett.8b02125. Epub 2018 Aug 27.

Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Kristina D Lacey  1 , Rashanique D Quarels  1 , Shaofu Du  1 , Ashley Fulton  1 , Nicholas J Reid  1 , Austin Firesheets  1 , Justin R Ragains  1
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Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Kristina D Lacey et al. Org Lett. .

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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