A catalytic method for chemoselective detritylation of 5'-tritylated nucleosides under mild and heterogeneous conditions using silica sulfuric acid as a recyclable catalyst

摘要

A rapid,mild and highly efficient procedure for the chemoselective deprotection of triphenylmethyl(trityl,Tr),p-anisyldi-phenylmethyl(monomethoxytrityl,MMT)and di-(p-anisyl)phenylmethyl(dimethoxytrityl,DMT)groups from nucleoside trityl ethers has been established.The deprotection was achieved at room temperature,using a catalytic amount of silica sulfuric acid(SSA)in acetonitrile.The trityl nucleosides were deprotected in 2-17 min without any depurination.These conditions are compatible with other acid sensitive hydroxyl protecting groups such as p-methoxybenzyl(PMB),isopropylidene,cyclohexylidene,di-(p-anisyl)methylidene,triisopropylsilyl(TIPS)and t-butyldimethylsilyl(TBDMS).