Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation

Ganesh Shrestha; Matteo Panza; Yashapal Singh; Nigam P. Rath; Alexei Demchenko

doi:10.1021/acs.joc.0c00943

Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation

Ganesh Shrestha, Matteo Panza, Yashapal Singh, Nigam P. Rath, Alexei Demchenko

University of Missouri-St. Louis

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

Abstract

The S -indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.

Original language	American English
Journal	Journal of Organic Chemistry
Volume	85
DOIs	https://doi.org/10.1021/acs.joc.0c00943
State	Published - 2020

Disciplines

Biochemistry, Biophysics, and Structural Biology

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title = "Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation",

abstract = " The S -indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis. ",

author = "Ganesh Shrestha and Matteo Panza and Yashapal Singh and Rath, {Nigam P.} and Alexei Demchenko",

year = "2020",

doi = "10.1021/acs.joc.0c00943",

language = "American English",

volume = "85",

journal = "Journal of Organic Chemistry",

}

TY - JOUR

T1 - Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation

AU - Shrestha, Ganesh

AU - Panza, Matteo

AU - Singh, Yashapal

AU - Rath, Nigam P.

AU - Demchenko, Alexei

PY - 2020

Y1 - 2020

N2 - The S -indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.

AB - The S -indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.

UR - https://doi.org/10.1021/ACS.JOC.0C00943

U2 - 10.1021/acs.joc.0c00943

DO - 10.1021/acs.joc.0c00943

M3 - Article

VL - 85

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation

Abstract

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