96013-93-3

Upstream product

• 96013-92-2 1-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-benzene 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 96013-92-2 1-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-benzene 

Relevant academic research and scientific papers

BiOClO4-mediated deprotection of silyl ethers

TES- and TBS-protected alcohols undergo deprotection in good to excellent yield upon heating with 1equiv of BiOClO4-xH2O in CH 2Cl2. TBDPS- and TIPS-protected 2°alcohols are more resistant to deprotection. The use of this method for selective desilylation is, however, limited to the deprotection of alkyl silyl ethers in the presence of TBDPS-protected phenols.

Mild deprotection of PMB ethers using tert-butyl bromide

A convenient and high yielding method for the cleavage and scavenging of p-methoxybenzyl protecting group of several alcohols using tert-butyl bromide in refluxing acetonitrile is described. Under these mild conditions other protecting groups such as acid sensitive allyl, benzyl, and Me3CPh2Si ethers, or isopropylidene acetals were unchanged. Interestingly, a selective alkoxy-PMB cleavage was observed in the presence of a PMB phenoxy ether.

A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with Selectfluor

A novel microwave-assisted, chemoselective and efficient method for the cleavage of silyl ethers (aliphatic and aromatic) catalyzed by Selectfluor is reported. A wide range of TBS-, TIPS-, and TBDPS-protected alkyl silyl ethers can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The chemoselective deprotection of phenolic TBS ethers, and not the TIPS- or TBDPS-protected phenolic ethers, and the deprotection of silyl esters were also achieved under these reaction conditions. In addition, the transetherification and etherification of benzylic hydroxy groups in alcoholic solvents is observed.

The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide

An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr. The Royal Society of Chemistry 2008.

Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol

Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time.

Highly Efficient and Convenient Deprotection of Methoxymethyl Ethers and Esters Using Bismuth Triflate in an Aqueous Medium

A simple and efficient method has been developed for the hydrolysis of methoxymethyl (MOM) ethers and esters to the corresponding alcohols and acids employing a catalytic amount of bismuth triflate in an aqueous medium. The conversions occur at ambient temperature and the yields of the deprotected alcohols are very good. The reaction was highly selective in the presence of other protecting groups such as TBDMS, TBDPS, benzyl, and allyl ethers.

Selective deprotection of alkyl vs. aryl silyl ethers

Alkyl silyl ethers, in particular t-butyldimethylsilyl derivatives, can be selectively cleaved in high yields over aryl silyl ethers using small percentage of I2 in MeOH at ambient temperatures.