Glycosylation intermediates studied using low temperature 1H- and 19F-DOSY NMR: new insight into the activation of trichloroacetimidates

Yan Qiao; Wenzhi Ge; Lingyu Jia; Xianglin Hou; Yingxiong Wang; Christian Marcus Pedersen

doi:10.1039/c6cc05272j

Glycosylation intermediates studied using low temperature ¹H- and ¹⁹F-DOSY NMR: new insight into the activation of trichloroacetimidates

Yan Qiao, Wenzhi Ge, Lingyu Jia, Xianglin Hou, Yingxiong Wang^*, Christian Marcus Pedersen

^*Corresponding author for this work

Department of Chemistry

15 Citations (Scopus)

116 Downloads (Pure)

Abstract

Low temperature ¹H- and ¹⁹F-DOSY have been used for analyzing reactive intermediates in glycosylation reactions, where a glycosyl trichloroacetimidate donor has been activated using different catalysts. The DOSY protocols have been optimized for low temperature experiments and provided new insight into acid catalyzed glycosylation chemistry. From the study a new glycosylation intermediate was characterized.

Original language	English
Journal	Chemical Communications
Volume	52
Issue number	76
Pages (from-to)	11418-11421
Number of pages	4
ISSN	1359-7345
DOIs	https://doi.org/10.1039/c6cc05272j
Publication status	Published - 2016

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10.1039/c6cc05272jLicence: CC BY-NC

Qiao_2016_Glycosylation_intermediatesFinal published version, 1.37 MBLicence: CC BY-NC

Cite this

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title = "Glycosylation intermediates studied using low temperature 1H- and 19F-DOSY NMR: new insight into the activation of trichloroacetimidates",

abstract = "Low temperature 1H- and 19F-DOSY have been used for analyzing reactive intermediates in glycosylation reactions, where a glycosyl trichloroacetimidate donor has been activated using different catalysts. The DOSY protocols have been optimized for low temperature experiments and provided new insight into acid catalyzed glycosylation chemistry. From the study a new glycosylation intermediate was characterized.",

author = "Yan Qiao and Wenzhi Ge and Lingyu Jia and Xianglin Hou and Yingxiong Wang and Pedersen, {Christian Marcus}",

year = "2016",

doi = "10.1039/c6cc05272j",

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T1 - Glycosylation intermediates studied using low temperature 1H- and 19F-DOSY NMR

T2 - new insight into the activation of trichloroacetimidates

AU - Qiao, Yan

AU - Ge, Wenzhi

AU - Jia, Lingyu

AU - Hou, Xianglin

AU - Wang, Yingxiong

AU - Pedersen, Christian Marcus

PY - 2016

Y1 - 2016

N2 - Low temperature 1H- and 19F-DOSY have been used for analyzing reactive intermediates in glycosylation reactions, where a glycosyl trichloroacetimidate donor has been activated using different catalysts. The DOSY protocols have been optimized for low temperature experiments and provided new insight into acid catalyzed glycosylation chemistry. From the study a new glycosylation intermediate was characterized.

AB - Low temperature 1H- and 19F-DOSY have been used for analyzing reactive intermediates in glycosylation reactions, where a glycosyl trichloroacetimidate donor has been activated using different catalysts. The DOSY protocols have been optimized for low temperature experiments and provided new insight into acid catalyzed glycosylation chemistry. From the study a new glycosylation intermediate was characterized.

U2 - 10.1039/c6cc05272j

DO - 10.1039/c6cc05272j

M3 - Letter

C2 - 27722642

AN - SCOPUS:84987889390

SN - 1359-7345

VL - 52

SP - 11418

EP - 11421

JO - Chemical Communications

JF - Chemical Communications

IS - 76

ER -

Glycosylation intermediates studied using low temperature 1H- and 19F-DOSY NMR: new insight into the activation of trichloroacetimidates

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Glycosylation intermediates studied using low temperature ¹H- and ¹⁹F-DOSY NMR: new insight into the activation of trichloroacetimidates