5-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)ethyl-1H-tetrazole | 1402832-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)ethyl-1H-tetrazole
• 英文别名: 5-[2-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]ethyl]-2H-tetrazole
• CAS: 1402832-59-0
• 化学式: C₂₉H₃₂N₄O₄
• 分子量: 500.597
• InChiKey: KKVOGKUBZGTSID-IXGYBEARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)ethyl-1H-tetrazole 在 吡啶 、 咪唑 、 10 wt% Pd(OH)2 on carbon 、 氟化氢吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 环己烯 为溶剂， 反应 7.17h， 生成
  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
• 作为产物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-aldehydo-D-altrohexofuranose 在 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 三乙胺盐酸盐 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 5-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)ethyl-1H-tetrazole
  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

• TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis
  作者：Hiroki Yoneyama、Naoki Oka、Yoshihide Usami、Shinya Harusawa

  DOI：10.1016/j.tetlet.2019.151517

  日期：2020.2

  Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 oC in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.

  各种腈与TMSN的处理3和卜2的Sn（OAc）2在30 ö下在苯60小时，得到相应的5-取代的1 ħ在良好-tetrazoles到优异的产率。该方法是温和有效的Wittenberger四唑合成的替代试剂系统，该系统在高温（93–110°C）下使用甲苯中的TMSN 3和Bu 2 SnO持续24–72 h。
• Efficient Transformation of Inactive Nitriles into 5-Substituted 1H-Tetrazoles Using Microwave Irradiation and Their Applications
  作者：Shinya Harusawa、Hiroki Yoneyama、Yoshihide Usami、Seiji Komeda

  DOI：10.1055/s-0032-1318476

  日期：——

  Efficient transformations of inactive nitriles into 5-substituted 1H-tetrazoles in DMF in a microwave reactor are described. The present method is applied to the synthesis of tetrazolato-bridged dinuclear platinum(II) complex and tetrazole C-1-ribonucleoside phosphoramidite.
• 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.