Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Kristina D Lacey; Rashanique D Quarels; Shaofu Du; Ashley Fulton; Nicholas J Reid; Austin Firesheets; Justin R Ragains

doi:10.1021/acs.orglett.8b02125

Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

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

Authors

Kristina D Lacey¹, Rashanique D Quarels¹, Shaofu Du¹, Ashley Fulton¹, Nicholas J Reid¹, Austin Firesheets¹, Justin R Ragains¹

Affiliation

¹ Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.

PMID: 30148367
DOI: 10.1021/acs.orglett.8b02125

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.