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Phenanthroline‐Catalyzed Stereoretentive Glycosylations
Author(s) -
Yu Fei,
Li Jiayi,
DeMent Paul M.,
Tu YiJung,
Schlegel H. Bernhard,
Nguyen Hien M.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201901346
Subject(s) - glycosylation , glycosidic bond , glycosyl donor , phenanthroline , glycosyl , chemistry , combinatorial chemistry , glycoside , glycoside hydrolase , catalysis , selectivity , stereochemistry , hydrolysis , enzyme , organic chemistry , biochemistry
Carbohydrates are essential moieties of many bioactive molecules in nature. However, efforts to elucidate their modes of action are often impeded by limitations in synthetic access to well‐defined oligosaccharides. Most of the current methods rely on the design of specialized coupling partners to control selectivity during the formation of glycosidic bonds. Reported herein is the use of a commercially available phenanthroline to catalyze stereoretentive glycosylation with glycosyl bromides. The method provides efficient access to α‐1,2‐ cis glycosides. This protocol has been performed for the large‐scale synthesis of an octasaccharide adjuvant. Density‐functional theory calculations, together with kinetic studies, suggest that the reaction proceeds by a double S N 2 mechanism.