How are TBDMS ethers and phenols deprotected?

This method enables deprotection of TBDMS ethers of primary alcohols in the presence of TBDMS ethers of secondary and tertiary alcohols and phenols. The silyl ethers of phenols were deprotected at longer reaction times. G. Sabitha, M. Syamala, J. S. Yadav, Org. Lett., 1999, 1, 1701-1703.

When was TBDMS-CL first used as a silylation agent?

When the commercially available tert -butyldimethylsilyl chloride (TBDMS-Cl) was initially used as a silylation agent, it was found by E. J. Corey ( J. Am. Chem. Soc. 1972, 94, 6192) to react very slowly and to give unsatisfactory yields with alcohols.

Which is the best way to cleave TBDMS ethers?

TBDMS ethers can be cleaved selectively in the presence of isopropylidine, Bn, Ac, Bz, THP, and TBDPS groups using tetrabutylammonium tribromide in methanol. This method is high yielding, fast, clean, safe, and cost-effective. R. Gopinath, B. K. Patel, Org. Lett., 2000, 2, 4177-4180.

Which is an efficient catalyst for chemoselective TBDMS ethers?

PMA supported on SiO 2 is found to be an efficient catalyst for the chemoselective, mild deprotection of TBDMS ethers. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N -Boc, N -Cbz, N -Fmoc, mesylate, and azide are tolerated.

How is TBAF used in the deprotection of silyl ethers?

The TBAF reagent has been used in the deprotection of all silyl ethers though the conditions will change depending on the nature of the silyl ether and its surrounding environment. A selection of some interesting and potentially useful examples of selective removal of one silyl ether in the presence of another are shown here.

Can a TBAF group be deprotected in the presence of AcOH?

TBAF, THF or 1:1 TBAF /AcOH, THF; TBDPS and TBS groups can be deprotected in the presence of one another under different conditions. ^ Corey, E. J.; Venkateswarlu, A. “Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives.”