[5-[2-[(2S,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]ethyl]tetrazol-2-yl]methyl 2,2-dimethylpropanoate | 1402832-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [5-[2-[(2S,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]ethyl]tetrazol-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1402832-73-8；1402832-78-3
• 化学式: C₅₀H₇₃N₆O₉PSi
• 分子量: 961.224
• InChiKey: JCJLIPNQZZGPOX-QWZSXUMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.0
• 重原子数：
  67
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-aldehydo-D-altrohexofuranose 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三乙胺盐酸盐 、 氟化氢吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 环己烯 为溶剂， 反应 12.67h， 生成 [5-[2-[(2S,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]ethyl]tetrazol-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM and POM groups for probing RNA catalysis

  摘要：

  Novel C5-linked C-0- and C-2-tetrazole ribonucleoside phosphoramidites were designed and synthesized via tetrazole C-nucleosides. Pivaloyloxymethyl (POM) and methyl-substituted POM (MePOM) groups were introduced as N-protecting groups in the tetrazole ring that can be readily removed under mild basic conditions. The phosphoramidites were successfully incorporated into the VS ribozyme substrate and hence providing a chemogenetic approach to determine which nucleobases of ribozymes function as the acid or base, in the studies of ribozyme general acid and base catalysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.082

文献信息

• Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM and POM groups for probing RNA catalysis
  作者：Shinya Harusawa、Hiroki Yoneyama、Daiki Fujisue、Masayoshi Nishiura、Mihoyo Fujitake、Yoshihide Usami、Zheng-yun Zhao、Scott A. McPhee、Timothy J. Wilson、David M.J. Lilley

  DOI：10.1016/j.tetlet.2012.08.082

  日期：2012.10

  Novel C5-linked C-0- and C-2-tetrazole ribonucleoside phosphoramidites were designed and synthesized via tetrazole C-nucleosides. Pivaloyloxymethyl (POM) and methyl-substituted POM (MePOM) groups were introduced as N-protecting groups in the tetrazole ring that can be readily removed under mild basic conditions. The phosphoramidites were successfully incorporated into the VS ribozyme substrate and hence providing a chemogenetic approach to determine which nucleobases of ribozymes function as the acid or base, in the studies of ribozyme general acid and base catalysis. (C) 2012 Elsevier Ltd. All rights reserved.