Tert-Butyl dimethylsilyl ether

Compound 158 is the starting material. This compound is first reduced with sodium borohydride to 159, and the resulting hydroxyl group is then protected as its tert-butyl dimethylsilyl ether (Scheme 7 49). The resulting compound 160 appears to possess the C-ring skeleton of baccatin HI. 

Quilliam, M.A., Ogilvie, K.K., Sadana, K.L., and Westmore, J.B., Study of rearrangement reactions occurring during gas chromatography of tert-butyl-dimethylsilyl ether derivatives of uridine, J. Chromatogr., 194, 379, 1980. 

Myher, J. J., Kuksis, A., Marai, L. and Yeung, S. K. F. (1978) Microdetermination of molecular species of oligo- and polyunsaturated diacylglycerols by gas chromatography-mass spectrometry of their tert-butyl dimethylsilyl ethers. Anal. Chem., 50, 557-61. 

The synthetic potential of silyl ethers as protecting groups for hydroxyls is based on the fact that they can be easily introduced and cleaved under mild conditions and their relative stability can be tuned by varying the substituents on silicon. In carbohydrate chemistry, the tert-butyl-dimethylsilyl (TBDMS), terl-butyldiphenylsilyl (TBDPS) and triethyl-silyl (TES) ethers are the most often applied silicon-based protecting groups (Scheme 2.9).23... 

---