Premium
Chemoselectivity in Self‐Promoted Glycosylation: N ‐ vs. O ‐Glycosylation
Author(s) -
Pinna Alessandro,
Pedersen Christian Marcus
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000526
Subject(s) - chemoselectivity , chemistry , glycosylation , nucleophile , anomer , sulfonamide , glycosyl , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry
Self‐promoted glycosylation using trichloroacetimidates and sulfonamides have recently been developed. In this communication, we study the parameters controlling the chemoselectivity between a nucleophilic sulfonamide nitrogen and an alcohol, both contained in the same molecule. The influence of solvent polarity and concentrations have been studied, and it has been revealed how the chemoselectivity, and to some extend the stereoselectivity, can be controlled. The experimental results furthermore provide insight into the reaction mechanism of this self‐promoted glycosylation and the mechanism of glycosylation reactions in general.