Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors.

Autor:	Lacey KD; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States., Quarels RD; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States., Du S; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States., Fulton A; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States., Reid NJ; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States., Firesheets A; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States., Ragains JR; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2018 Sep 07; Vol. 20 (17), pp. 5181-5185. Date of Electronic Publication: 2018 Aug 27.
DOI:	10.1021/acs.orglett.8b02125
Abstrakt:	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.
Databáze:	MEDLINE
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