Tert-Butyldimethylsilyl Chloride

     Tert-Butyldimethylsilyl chloride is a silanizing agent. Derivatization reagents are used for analysis and preparation. Protect tertiary alcohols. Reacts with alcohols to form silicon ethers. Determining the conformation of cholesterol derivatives. Tert-Butyldimethylsilyl chloride is one of the most widely used important protective groups in organic synthesis. It can react with hydroxyl groups under mild conditions to form the corresponding silicon ethers, and react with ketones, esters or amides to form the corresponding enol silicon ethers. The reaction between TBDMSCl and alcoholic hydroxyl groups to form silicon ethers is particularly important. Compared with TMS protecting groups, their preparation conditions are basically the same, but the chemical stability of TBDMS silyl ether is many times higher than that of TMS silyl ether. Therefore, TBDMSCl has a wider application range in this aspect, and the product yield is generally higher. The reaction of this reagent with hydroxyl groups can usually be carried out in CH2Cl2, THF or DMF, and imidazole, pyridine and Et3N can be used as bases. DMAP is often used as a catalyst, but if Et3N is used as the base in the reaction, a DMAP catalyst is required. The selectivity of this reaction on polyhydroxy substrates is related to the solvent and alkali catalyst used. The CH2Cl2-Et3N-DMAP combination has the best selectivity and can be easily achieved against primary alcohols in the presence of secondary or tertiary alcohols. selective protection. The reaction between TBDMSCl and phenolic hydroxyl groups is very similar to that of alcoholic hydroxyl groups, but the reaction temperature needs to be higher. Whether it is a silicon ether generated from an alcoholic hydroxyl group or a phenolic hydroxyl group, the conditions for removing protecting groups are basically the same.

1. Used as an auxiliary raw material for the synthesis of prostaglandins, certain antibiotics, and the hypolipidemic drugs lovastatin and simvastatin.

2. Used as pharmaceutical intermediates and organic synthesis, as a hydroxyl protecting agent in organic synthesis

3. Silanizing agent. In organic synthesis, it is used as a hydroxyl protecting agent and derivatization reagent for analysis and preparation. Protect tertiary alcohols. Reacts with alcohols to form silicon ethers. Determining the conformation of cholesterol derivatives. Synthetic prostaglandins, auxiliary raw materials for certain antibiotics and the anti-hyperlipidemic drugs Lovastatin and Simvastatin.

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