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

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• 作者：Ali Khalafi-Nezhad ; Abolfath Parhami ; Mohammad Navid Soltani Rad ; Mohammad Ali Zolfigol ; Abdolkarim Zare
• 关键词：Detritylation ; Nucleoside ; Trityl ; Heterogeneous ; Silica sulfuric acid
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：23 July 2007
• 卷：48
• 期：30
• 页码：5219-5222
• 文件大小：135 K

摘要

A rapid, mild and highly efficient procedure for the chemoselective deprotection of triphenylmethyl (trityl, Tr), p-anisyldiphenylmethyl (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).