Chemical Properties
Colorless liquid
Physical properties
bp 70°C/0.5 mmHg; d 0.986 g cm?3.
Uses
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane can be used as simultaneous protection of the 3'- and 5'-hydroxyl functions of
furanose nucleosides;protecting group for carbohydrates;3,4
protecting group reagent for open-chain polyhydroxy compounds;
preparation of cyclic bridged peptides.
The reagent
design was based upon the fact that triisopropylsilyl chloride
reacts 1000 times faster with primary alcohols than secondary
alcohols. Thus in the case of 3',5'-dihydroxy nucleosides the
reagent initially silylates at the 5'-position. This is then followed
by intramolecular reaction with the secondary alcohol at the
3'-position to give the doubly protected derivative (eq 1).
Uses
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is used in the analysis of Watson-Crick and Hoogstein base pairing in nucleotides. Also used in the formation of ribavirin chemical delivery systems.
Uses
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.
Preparation
can be prepared starting from trichlorosilane
by treatment with i-PrMgCl, H2O, and acetyl chloride.
Alternatively, it can be prepared by the reaction of 1,1,3,3-
tetraisopropyldisiloxane with CCl4 in the presence of catalytic
PdCl2.This method is also suitable for its in situ preparation.
