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.
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Applications
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.
Solubility
Miscible with dimethylformamide, hexane, ethyl acetate, chloroform and dichloromethane.
Notes
Incompatible with strong oxidizing agents and water.
RUO – Research Use Only
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.