Dimethylthiocarbamate (DMTC): An Alcohol Protecting Group

D. K. Barma, A. Bandyopadhyay, Jorge H. Capdevila, J. R. Falck

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Abstract

(Equation Presented) Dimethylthiocarbamates (DMTCs), prepared from the corresponding alcohols using commercial dimethylthiocarbamoyl chloride, are spectrally simple, achiral, and nonpolar. DMTCs are moderately to highly stable to a wide range of reagents and conditions including metal hydrides, hydroboration, ylides, NaOH, HCl, organolithiums, Grignards, DDQ, PCC, Swern, n-Bu4NF, CrCl2, heat, and Lewis acids. They are readily removed by NalO4 or H2O2 in the presence of other common alcohol protecting groups.

Original languageEnglish (US)
Pages (from-to)4755-4757
Number of pages3
JournalOrganic Letters
Volume5
Issue number25
DOIs
Publication statusPublished - Dec 11 2003

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ASJC Scopus subject areas

  • Molecular Medicine

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