Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides

A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to giv...

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Bibliographic Details
Main Authors: Tatina, Madhu Babu, Xia, Mengxin, Rao, Peilin, Judeh, Zaher M. A.
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2020
Subjects:
Engineering::Chemical engineering
C-, O-, N- And S-linked Glycosides
Enosides
Online Access:https://hdl.handle.net/10356/137429
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Institution: Nanyang Technological University
Language: English
Description
Summary:A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.

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