Ababuctz nle selective clesvage ofprimary sml secondsty trimethylsilyl (TMS). abopmpylsilyl (TIPS), tut-butyldimahylsilyl~DMS)rrndtut-butyldiphnylsilyl~DPS)ahaswithwrtral~urminr\mdaverymildconditions is described. The method involvea tdiktkm of the support, pwiously activated by hesting at WC/O. 1 torr fat 16 h snd Later deactivated with vsriable emouotsofwrter(l.54.5%),in5o:lntio~~n~toth~~intbe prrsareofnon-polr~~;lih:haune.ThedeprobctionrPbdependsontbesrericbull6nessoftbesilicon suwtuents, following the order TMS > > TBDMS rTIPS>TBDPS,asweUrsonthetyptoftbeatElchdcsrbon. ~proccdurt~~sfliminatebetweendi&rrntsilylgroupslocatcdatequivrlenrpogitioapofthesamemolecule sfbding the cotwpootling monopIotected slcohols in very good yields.
Derivatization of alcohols as silyl ethers is a widely used method of protection in organic chemistry'.
In this regard, selective deprotecdon of silyl ethers in the presence of other silyl protecting groups or acidsensitive moieties is of tremendous utility to the synthetic chemist. A variety of methods to cleave silylprotected alcohols have been reported, being mostly thoee which utilize fluoride ion due to the high affinity