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

22 Scopus citations

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	English (US)
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

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b02125

Cite this

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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.",

author = "Lacey, \{Kristina D.\} and Quarels, \{Rashanique D.\} and Shaofu Du and Ashley Fulton and Reid, \{Nicholas J.\} and Austin Firesheets and Ragains, \{Justin R.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = sep,

day = "7",

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

language = "English (US)",

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pages = "5181--5185",

journal = "Organic Letters",

issn = "1523-7060",

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TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/85052858584

UR - https://www.scopus.com/pages/publications/85052858584#tab=citedBy

U2 - 10.1021/acs.orglett.8b02125

DO - 10.1021/acs.orglett.8b02125

M3 - Article

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AN - SCOPUS:85052858584

SN - 1523-7060

VL - 20

SP - 5181

EP - 5185

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Abstract

All Science Journal Classification (ASJC) codes

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