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1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is a silylating reagent used for simultaneous protection of 3'- and 5'-hydroxy functions of ribonucleosides. It is used in the analysis of Watson-Crick and Hoogstein base pairing in nucleotides. It is also employed in the formation of ribavirin chemical delivery systems. Further, it serves as a protecting group reagent for open-chain polyhydroxy compounds. In addition to this, it is involved in the preparation of cyclic bridged peptides.
Reagent for the protection of diols, including carbohydrate-type molecules, as their 1,3-(1,1,3,3-tetraisopropyldisiloxanylidene) (TIPDS) derivatives, formed in the presence of imidazole: J. Chem. Res. Synop., 24 (1979); J. Org. Chem., 50, 1651 (1985), or pyridine-DMF: Tetrahedron, 41, 4545, 4557 (1985). The high steric demand of the TIPDS group enables discrimination between primary and secondary OH. It is readily cleaved by F- (e.g. TBAF in THF) or by aqueous acid or base. See Appendix 4.
Osawa, T.; Hari, Y.; Dohi, M.; Matsuda, Y.; Obika, S. Synthesis and Properties of the 5-Methyluridine Derivative of 3,4-Dihydro-2H-pyran-Bridged Nucleic Acid (DpNA). J. Org. Chem. 2015, 80 (21), 10474-10481.
Clobes, C.; Jerabek, P.; Nußbruch, I.; Frenking, G.; von Hänisch, C. Stepwise Synthesis of Siloxane-Substituted Oligoarsanes and Structural Investigation of Alkaline Earth Metal Derivatives. Eur. J. Inorg. Chem. 2015, 2015 (20), 3264-3273.
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
Do not breathe dusts or mists. 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.