Issue 10, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 dec 2019
Accepted
17 feb 2020
First published
17 feb 2020

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

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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