Regenerative Glycosylation

Yashapal Singh; Tinghua Wang; Scott A. Geringer; Keith Stine; Alexei V. Demchenko

doi:10.1021/acs.joc.7b02768

Regenerative Glycosylation

Yashapal Singh, Tinghua Wang, Scott A. Geringer, Keith Stine, Alexei V. Demchenko

University of Missouri-St. Louis

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

Abstract

Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

Original language	American English
Journal	The Journal of Organic Chemistry
Volume	83
DOIs	https://doi.org/10.1021/acs.joc.7b02768
State	Published - Dec 11 2017

Keywords

Carbohydrates
Free radicals
Alkyls
Post-translational modification
Anions

Disciplines

Biochemistry, Biophysics, and Structural Biology
Biochemistry
Chemistry

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title = "Regenerative Glycosylation",

abstract = " Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.",

keywords = "Carbohydrates, Free radicals, Alkyls, Post-translational modification, Anions",

author = "Yashapal Singh and Tinghua Wang and Geringer, {Scott A.} and Keith Stine and Demchenko, {Alexei V.}",

note = "Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series.",

year = "2017",

month = dec,

day = "11",

doi = "10.1021/acs.joc.7b02768",

language = "American English",

volume = "83",

journal = "The Journal of Organic Chemistry",

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TY - JOUR

T1 - Regenerative Glycosylation

AU - Singh, Yashapal

AU - Wang, Tinghua

AU - Geringer, Scott A.

AU - Stine, Keith

AU - Demchenko, Alexei V.

N1 - Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series.

PY - 2017/12/11

Y1 - 2017/12/11

N2 - Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

AB - Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

KW - Carbohydrates

KW - Free radicals

KW - Alkyls

KW - Post-translational modification

KW - Anions

UR - https://pubs.acs.org/doi/10.1021/acs.joc.7b02768

UR - https://pubs.acs.org/doi/10.1021/acs.joc.7b02768#

U2 - 10.1021/acs.joc.7b02768

DO - 10.1021/acs.joc.7b02768

M3 - Article

VL - 83

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

ER -

Regenerative Glycosylation

Abstract

Keywords

Disciplines

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