Iodine and its interhalogen compounds:Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation

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Cura, P., Aloui, M., Ravindranathan Kartha, K. P. and Field, R. A. ORCID: https://orcid.org/0000-0001-8574-0275 (2000) Iodine and its interhalogen compounds:Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation. Synlett (9). pp. 1279-1280. ISSN 0936-5214

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Abstract

The reactivity of O-benzylated 1-thio-β-D-galactopyranosides in iodine-promoted methanolysis reactions was shown to correlate with aglycone structure, as expected (R = p.NO2Ph < Ph < Bn < p.MeOPh < Me). The rate of methanolysis could be altered substantially through appropriate choice of promoter (ICl > IBr ~ I2+DDQ > I2), with even the unreactive nitrophenyl thioglycoside undergoing complete reaction in less than 2 minutes in acetonitrile in the presence of ICl.

Item Type: Article
Uncontrolled Keywords: glycosylation,iodine,thioglycosides,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1605
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
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Depositing User: LivePure Connector
Date Deposited: 11 Sep 2024 09:30
Last Modified: 18 Jun 2026 20:21
URI: https://ueaeprints.uea.ac.uk/id/eprint/96687
DOI:

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