2',3',5'-tri-O-tetra(4-methylbenzoyl)cytidine | 863592-03-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3',5'-tri-O-tetra(4-methylbenzoyl)cytidine
• 英文别名: Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-5)]Ribf(b)-cytosin-1-yl；[(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 863592-03-4
• 化学式: C₃₃H₃₁N₃O₈
• 分子量: 597.624
• InChiKey: AZAIJBGWTJLOTL-YXINZVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-tetra(4-methylbenzoyl)cytidine 在 正丁基锂 、 2,2,2-三氟乙醇 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以66%的产率得到5'-O-(4-methylbenzoyl)cytidine
  参考文献：
  名称：

  Selective Removal of the 2‘- and 3‘-O-Acyl Groups from 2‘,3‘,5‘-Tri-O-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹

  摘要：

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.

  DOI：

  10.1021/jo0600104
• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-[4-[(dibutylamino)methylideneamino]-2-oxopyrimidin-1-yl]-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate 在 水 、 1-羟基苯并三唑 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到2',3',5'-tri-O-tetra(4-methylbenzoyl)cytidine
  参考文献：
  名称：

  Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions

  摘要：

  Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced Into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.

  DOI：

  10.1021/ol100676j

文献信息

• Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹
  作者：Ireneusz Nowak、Martin Conda-Sheridan、Morris J. Robins

  DOI：10.1021/jo051256w

  日期：2005.9.1

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.
• Selective Removal of the 2‘- and 3‘-<i>O</i>-Acyl Groups from 2‘,3‘,5‘-Tri-<i>O</i>-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹
  作者：Ireneusz Nowak、Carl T. Jones、Morris J. Robins

  DOI：10.1021/jo0600104

  日期：2006.4.1

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.
• Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions
  作者：Akihiro Ohkubo、Yasukazu Kuwayama、Yudai Nishino、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ol100676j

  日期：2010.6.4

  Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced Into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.