Dimethylthiocarbamate (DMTC): an alcohol protecting group.
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-Bu(4)NF, CrCl(2), heat, and Lewis acids. They are readily removed by NaIO(4) or H(2)O(2) in the presence of other common alcohol protecting groups. [structure: see text]
Barma
D K
DK
Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA.
Bandyopadhyay
A
A
Capdevila
Jorge H
JH
Falck
J R
JR
D000438:Alcohols / Q000737:chemistry*; D015394:Molecular Structure; D013859:Thiocarbamates / Q000737:chemistry*
D000438:Alcohols; D013859:Thiocarbamates; C492476:dimethylthiocarbamoyl chloride