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      Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

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          Summary

          A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2- trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.

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          Tertiary Phosphane/Tetrachloromethane, a Versatile Reagent for Chlorination, Dehydration, and P?N Linkage

          Rolf Appel (1975)
          Article 0 comments Cited 92 times – based on 0 reviews     Review now
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            Recent progress in O-glycosylation methods and its application to natural products synthesis

            Kazunobu Toshima, Kuniaki TATSUTA (1993)
            Article 0 comments Cited 72 times – based on 0 reviews     Review now
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              A study of 13CH coupling constants in hexopyranoses

              Klaus Bock, Christian Pedersen (1974)
              Article 0 comments Cited 68 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Anup Kumar Misra
                Sabine Flitsch: Role: Associate Editor
                Journal
                Journal ID (nlm-ta): Beilstein J Org Chem
                Journal ID (iso-abbrev): Beilstein J Org Chem
                Title: Beilstein Journal of Organic Chemistry
                Publisher: Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                ISSN (Electronic): 1860-5397
                Publication date Collection: 2013
                Publication date (Electronic): 22 May 2013
                Volume: 9
                Pages: 974-982
                Affiliations
                [1 ]Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata-700054, India, Fax: 91-33-2355 3886
                Article
                DOI: 10.3762/bjoc.9.112
                PMC ID: 3678522
                PubMed ID: 23766814
                SO-VID: 8e4f2fb0-ef59-4d79-ad7f-f87d306b0f2e
                Copyright © Copyright © 2013, Ghosh et al; licensee Beilstein-Institut.
                License:

                This is an Open Access article 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.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                Date received : 12 March 2013
                Date accepted : 29 April 2013
                Categories
                Subject: Full Research Paper
                Subject: Chemistry
                Subject: Organic Chemistry

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: appel reagent,carbon tetrabromide,glycosyl hemiacetal,glycosyl thiol,thioglycoside,triphenylphosphine
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: appel reagent, carbon tetrabromide, glycosyl hemiacetal, glycosyl thiol, thioglycoside, triphenylphosphine

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