96013-93-3Relevant articles and documents
BiOClO4-mediated deprotection of silyl ethers
Crouch, R. David,Romany, Candice A.,Kreshock, Anna C.,Menconi, Karina A.,Zile, Jennifer L.
, p. 1279 - 1281 (2004)
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.
A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with Selectfluor
Shah, Syed Tasadaque A.,Singh, Surendra,Guiry, Patrick J.
experimental part, p. 2179 - 2182 (2009/07/01)
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.
Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
Yeom, Chang-Eun,Kim, Young Jong,Lee, So Young,Shin, Yong Je,Kim, B. Moon
, p. 12227 - 12237 (2007/10/03)
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.