The Preparation and Synthetic Utility of tert-Butyldiphenylsilyl Ethers

The utility of tert-butyldiphenylsilyl chloride as a reagent for the protection of hydroxyl groups was explored. The corresponding tert-BDPSi ethers have much greater stability to acids, and under conditions of hydrogenolysis, than related silyl and trityl ethers. Preferential removal of trityl, tetrahydropyranyl, benzyl, and other silyl ethers and acetals can be effected in presence of tert-EDPSi ethers. Treatment with fluoride ion causes smooth cleavage of the latter.