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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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
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spelling sg-ntu-dr.10356-1374292023-12-29T06:53:50Z Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides Tatina, Madhu Babu Xia, Mengxin Rao, Peilin Judeh, Zaher M. A. School of Chemical and Biomedical Engineering Engineering::Chemical engineering C-, O-, N- And S-linked Glycosides Enosides 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. Published version 2020-03-25T05:19:26Z 2020-03-25T05:19:26Z 2019 Journal Article Tatina, M. B., Xia, M., Rao, P., & Judeh, Z. M. A. (2019). Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides. Beilstein Journal of Organic Chemistry, 15, 1275-1280. doi:10.3762/bjoc.15.125 1860-5397 https://hdl.handle.net/10356/137429 10.3762/bjoc.15.125 31293675 2-s2.0-85068340494 15 1275 1280 en Beilstein Journal of Organic Chemistry © 2019 Tatina et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc). The definitive version of this article is the electronic one which can be found at: doi:10.3762/bjoc.15.125 application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Engineering::Chemical engineering
C-, O-, N- And S-linked Glycosides
Enosides
spellingShingle Engineering::Chemical engineering
C-, O-, N- And S-linked Glycosides
Enosides
Tatina, Madhu Babu
Xia, Mengxin
Rao, Peilin
Judeh, Zaher M. A.
Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
description 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.
author2 School of Chemical and Biomedical Engineering
author_facet School of Chemical and Biomedical Engineering
Tatina, Madhu Babu
Xia, Mengxin
Rao, Peilin
Judeh, Zaher M. A.
format Article
author Tatina, Madhu Babu
Xia, Mengxin
Rao, Peilin
Judeh, Zaher M. A.
author_sort Tatina, Madhu Babu
title Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
title_short Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
title_full Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
title_fullStr Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
title_full_unstemmed Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
title_sort robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated o-, c-, n- and s-linked glycosides
publishDate 2020
url https://hdl.handle.net/10356/137429
_version_ 1787136799398690816

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