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

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

Research output: Contribution to journal › Article › peer-review

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.

Original language	American English
Pages (from-to)	5181-5185
Number of pages	5
Journal	Organic letters
Volume	20
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.8b02125
State	Published - Sep 7 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b02125

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title = "Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors",

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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doi = "10.1021/acs.orglett.8b02125",

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T1 - Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

AU - Lacey, Kristina D.

AU - Quarels, Rashanique D.

AU - Du, Shaofu

AU - Fulton, Ashley

AU - Reid, Nicholas J.

AU - Firesheets, Austin

AU - Ragains, Justin R.

PY - 2018/9/7

Y1 - 2018/9/7

N2 - 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.

AB - 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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Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Abstract

ASJC Scopus subject areas

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