Tetrabutylammonium Tribromide (TBATB)−MeOH: An efficient chemoselective reagent for the cleavage of Tert-Butyldimethylsilyl (TBDMS) ethers

TBDMS, THP and DMT ethers are efficiently deprotected with tetrabutylammonium tribromide in methanol. The apparent order of stability of different protecting group is phenolic TBDMS > 1° OTBDPS > 2° OTBDMS > 2° OTHP > 1° OTHP > 1° OTBDMS > 1° ODMT. TBDMS ether has been cleaved selectively in the presence of isopropylidine, Bn, Ac, Bz, THP and TBDPS groups. This method is high yielding, fast, clean, safe, cost-effective and therefore most suitable for practical organic synthesis