Issue 10, 2020
From the journal:

Organic & Biomolecular Chemistry

α-Selective glycosylations using glycosyl N-(ortho-methoxyphenyl)trifluoroacetimidates†

Karolina Kowalskaab  and  Christian Marcus Pedersen ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark
E-mail: cmp@chem.ku.dk

b Faculty of Chemistry, Adam Mickiewicz University in Poznań, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland

Abstract

Six N-(o-methoxyphenyl)trifluoroacetimidate glycosyl donors have been synthesized and their role as glycosyl donors has been investigated. The donors were synthesized with complete β-selectivity, except in one case, and were found to be stable. When Bi(OTf)3, Fe(OTf)2, and Zn(OTf)2 were employed as catalysts, the glycosylations were found to be highly α-selective in Et2O. The selectivity and reaction rate changed with a change in the acceptor reactivity.

Graphical abstract: α-Selective glycosylations using glycosyl N-(ortho-methoxyphenyl)trifluoroacetimidates

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Article information

DOI
https://doi.org/10.1039/C9OB02696G
Article type
Paper
Submitted
19 Dec 2019
Accepted
17 Feb 2020
First published
17 Feb 2020

Org. Biomol. Chem., 2020,18, 1918-1925

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α-Selective glycosylations using glycosyl N-(ortho-methoxyphenyl)trifluoroacetimidates

K. Kowalska and C. M. Pedersen, Org. Biomol. Chem., 2020, 18, 1918 DOI: 10.1039/C9OB02696G

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