Ceric Ammonium Nitrate on Silica Gel for Efficient and Selective Removal of Trityl and Silyl Groups

Ceric Ammonium Nitrate on Silica Gel for Efficient and Selective Removal of Trityl and Silyl Groups

Silica gel-supported ceric ammonium nitrate (CAN−SiO2) was found effective for rapid and selective cleavage of trityl (Tr), monomethoxytrityl (MMTr), and dimethoxytrityl (DMTr) groups from protected nucleosides and nucleotides under mild conditions. Efficiency of deprotections depended upon the stab...

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Veröffentlicht in:Journal of organic chemistry 2000-08, Vol.65 (17), p.5077-5088
Hauptverfasser: Hwu, Jih Ru, Jain, Moti L, Tsai, Fu-Yuan, Tsay, Shwu-Chen, Balakumar, Arumugham, Hakimelahi, Gholam H
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container_end_page 5088
container_issue 17
container_start_page 5077
container_title Journal of organic chemistry
container_volume 65
creator Hwu, Jih Ru
Jain, Moti L
Tsai, Fu-Yuan
Tsay, Shwu-Chen
Balakumar, Arumugham
Hakimelahi, Gholam H
description Silica gel-supported ceric ammonium nitrate (CAN−SiO2) was found effective for rapid and selective cleavage of trityl (Tr), monomethoxytrityl (MMTr), and dimethoxytrityl (DMTr) groups from protected nucleosides and nucleotides under mild conditions. Efficiency of deprotections depended upon the stability of the resultant carbocationic species:  DMTr+ > MMTr+ > Tr+. Use of a catalytic amount of this solid-supported reagent can also efficiently and selectively remove the tert-butyldimethylsilyl or the triisopropylsilyl group from a primary hydroxyl functionality in di- or trisilyl ethers of ribonucleosides. A comparative study of deprotection reactions by utilization of CAN alone or CAN−SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN−SiO2 in the removal of these protective groups from organic molecules.
doi_str_mv 10.1021/jo000024o
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A comparative study of deprotection reactions by utilization of CAN alone or CAN−SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN−SiO2 in the removal of these protective groups from organic molecules.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>10993330</pmid><doi>10.1021/jo000024o</doi><tpages>12</tpages></addata></record>
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title Ceric Ammonium Nitrate on Silica Gel for Efficient and Selective Removal of Trityl and Silyl Groups
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