I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Triisopropylsilyl trifluoromethanesulfonate is used as a reagent for the introduction of triisopropylsilyl(TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.
Reagent for introduction of the triisopropylsilyl (TIPS) group: Tetrahedron Lett., 22, 3455 (1981); compare Chlorotriisopropylsilane, A17376, and Appendix 4. For general reactions of silyl triflates, see Trimethylsilyl trifluoromethanesulfonate, A12535.
For use in the synthesis of 2-substituted benzothiopyran-4-ones, see: Synlett, 182 (1996):
A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with TIPS-OTf, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).
For a comprehensive review of the TIPS group in organic chemistry, see: Chem. Rev., 95, 1009 (1995).
Hayashi, Y.; Yamazaki, T.; Nakanishi, Y.; Ono, T.; Taniguchi, T.; Monde, K.; Uchimaru, T. Asymmetric Nitrocyclopropanation of alfa-Substituted alfa, beta-Enals Catalyzed by Diphenylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereogenic Centers. Eur. J. Org. Chem. 2015, 2015 (26), 5747-5754.
Chang, J. C.; Lai, C. C.; Chiu, S. H. A Redox-Controllable Molecular Switch Based on Weak Recognition of BPX26C6 at a Diphenylurea Station. Molecules 2015, 20 (2), 1775-1787.
Gefahrenhinweise (EU): H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.