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Synlett 2000; 2000(9): 1279-1280
DOI: 10.1055/s-2000-7152
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Iodine and its Interhalogen Compounds: Versatile Reagents in Carbohydrate Chemistry XII. Tuning Promoter Reactivity for Thioglycoside Activation

Peter Cura* , Mahmoud Aloui, K. P. Ravindranathan Kartha, Robert A. Field
  • *School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK; Fax +44 (13 34) 46 38 08; E-mail: raf2@st-and.ac.uk
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Publication Date:
31 December 2000 (online)

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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.

iodine - glycosylation - thioglycosides

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