Fascione, MA and Turnbull, WB (2010) Benzyne arylation of oxathiane glycosyl donors. Beilstein Journal of Organic Chemistry, 6. ISSN 1860-5397
Abstract
The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2010 Fascione et al. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
Keywords: | benzyne, 1,2-cis-glycosides, glycosyl acetates, oxathiane glycosyl donors, stereoselective glycosylations, intramolecular aglycon delivery, lead tetra-Acetate, oligosaccharide synthesis, oxidation, 1-aminobenzotriazole, thioglycosides, recognition, strategy, cancer, cells |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 14 Feb 2013 13:50 |
Last Modified: | 26 Oct 2016 02:58 |
Published Version: | http://dx.doi.org/10.3762/bjoc.6.19 |
Status: | Published |
Publisher: | Beilstein Institute |
Refereed: | Yes |
Identification Number: | 10.3762/bjoc.6.19 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:74917 |