Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds 1, 2
…, P Cura, M Aloui, SK Readman, TJ Rutherford…
Index: Kartha, K.P. Ravindranathan; Cura, Peter; Aloui, Mahmoud; Readman, S. Kristy; Rutherford, Trevor J.; Field, Robert A. Tetrahedron Asymmetry, 2000 , vol. 11, # 2 p. 581 - 593
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Citation Number: 39
Abstract
Treatment of 'armed'methyl thiogalactosides with iodine in the absence of an acceptor alcohol results in thioglycoside epimerisation, whereas there is no effect on the corresponding 'disarmed'methyl thioglycosides. In contrast, iodine–hexamethyldisilane (which generates iodotrimethylsilane in situ) brings about epimerisation of 'disarmed' thioglycosides, ultimately giving rise to the corresponding α-glycosyl iodides on extended ...
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