[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxo-4-[4-(3,4,5-trioctadecoxybenzoyl)piperazin-1-yl]butanoate | 1380432-99-4

• 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: [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxo-4-[4-(3,4,5-trioctadecoxybenzoyl)piperazin-1-yl]butanoate
• CAS: 1380432-99-4
• 化学式: C₁₀₀H₁₅₆N₄O₁₃
• 分子量: 1622.36
• InChiKey: GCQZXWSQNLNYRU-SFINRJCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.9
• 重原子数：
  117
• 可旋转键数：
  69
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  181
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxo-4-[4-(3,4,5-trioctadecoxybenzoyl)piperazin-1-yl]butanoate 在 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以99%的产率得到[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxo-4-[4-(3,4,5-trioctadecoxybenzoyl)piperazin-1-yl]butanoate
  参考文献：
  名称：

  Liquid-Phase RNA Synthesis by Using Alkyl-Chain-Soluble Support

  摘要：

  AbstractRecent progress in the RNA therapeutics has increased demand for the synthesis of large quantities of oligoribonucleotides. The assembly of RNA oligomers relies mainly on solid‐phase approaches. These allow rapid product purification and the ability to drive a target reaction to completion through the use of excess reagents. Despite the known advantages of solid‐phase synthesis, some issues in the process remain to be addressed, such as low and limited scale, reagent accessibility, and the use of a very large excess of reagents. Herein, we report a highly efficient and practical method of liquid‐phase synthesis of RNA oligomers by using alkyl‐chain‐soluble support. We demonstrate the utility of the liquid‐phase method through 21‐mer RNA synthesis on a gram scale.

  DOI：

  10.1002/chem.201300655
• 作为产物：
  描述：

  piperazin-1-yl(3,4,5-tris(octadecyloxy)phenyl)methanone hydrochloride 、 5-O-(4,4-二甲氧基三苯基甲基)-胸苷-3-O-丁二酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以98%的产率得到[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxo-4-[4-(3,4,5-trioctadecoxybenzoyl)piperazin-1-yl]butanoate
  参考文献：
  名称：

  Liquid-Phase RNA Synthesis by Using Alkyl-Chain-Soluble Support

  摘要：

  AbstractRecent progress in the RNA therapeutics has increased demand for the synthesis of large quantities of oligoribonucleotides. The assembly of RNA oligomers relies mainly on solid‐phase approaches. These allow rapid product purification and the ability to drive a target reaction to completion through the use of excess reagents. Despite the known advantages of solid‐phase synthesis, some issues in the process remain to be addressed, such as low and limited scale, reagent accessibility, and the use of a very large excess of reagents. Herein, we report a highly efficient and practical method of liquid‐phase synthesis of RNA oligomers by using alkyl‐chain‐soluble support. We demonstrate the utility of the liquid‐phase method through 21‐mer RNA synthesis on a gram scale.

  DOI：

  10.1002/chem.201300655

文献信息

• Liquid-Phase RNA Synthesis by Using Alkyl-Chain-Soluble Support
  作者：Shokaku Kim、Masanori Matsumoto、Kazuhiro Chiba

  DOI：10.1002/chem.201300655

  日期：2013.6.24

  AbstractRecent progress in the RNA therapeutics has increased demand for the synthesis of large quantities of oligoribonucleotides. The assembly of RNA oligomers relies mainly on solid‐phase approaches. These allow rapid product purification and the ability to drive a target reaction to completion through the use of excess reagents. Despite the known advantages of solid‐phase synthesis, some issues in the process remain to be addressed, such as low and limited scale, reagent accessibility, and the use of a very large excess of reagents. Herein, we report a highly efficient and practical method of liquid‐phase synthesis of RNA oligomers by using alkyl‐chain‐soluble support. We demonstrate the utility of the liquid‐phase method through 21‐mer RNA synthesis on a gram scale.