69304-37-6

Colorless liquid

bp 70°C/0.5 mmHg; d 0.986 g cm?3.

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).

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.

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.