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Issue 28, 2017
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Regioselective SN2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis

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Abstract

Triflates of myo-inositol undergo facile solvolysis in DMSO and DMF yielding SN2 products substituted with O-nucleophiles; DMF showed slower kinetics. Axial O-triflate undergoes faster substitution than equatorial O-triflate. By exploiting this difference in kinetics, solvent-tuning and sequence-controlled nucleophilysis, rapid synthesis of three azido-inositols of myo-configuration from myo-inositol itself has been achieved.

Graphical abstract: Regioselective SN2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis

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Publication details

The article was received on 15 Feb 2017, accepted on 10 Mar 2017 and first published on 10 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01219E
Citation: Chem. Commun., 2017,53, 3971-3973
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    Regioselective SN2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis

    A. Ravi, S. Z. Hassan, A. N. Vanikrishna and K. M. Sureshan, Chem. Commun., 2017, 53, 3971
    DOI: 10.1039/C7CC01219E

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