2',3',5'-tri-O-tetraisobutyrylcytidine | 863592-02-3

• 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-tetraisobutyrylcytidine
• 英文别名: 2',3',5'-tri-O-isobutyrylcytidine；isobutyryl(-2)[isobutyryl(-3)][isobutyryl(-5)]Ribf(b)-cytosin-1-yl；[(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
• CAS: 863592-02-3
• 化学式: C₂₁H₃₁N₃O₈
• 分子量: 453.492
• InChiKey: LXVIIZSREYEJFA-MWQQHZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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-tetraisobutyrylcytidine 在 正丁基锂 、 2,2,2-三氟乙醇 作用下， 以 吡啶 、 正己烷 为溶剂， 反应 0.5h， 生成 5'-O-isobutyryl-4-N-tritylcytidine
  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：

  胞苷 在 吡啶 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 14.0h， 生成 2',3',5'-tri-O-tetraisobutyrylcytidine
  参考文献：
  名称：

  Hydrothermal Deamidation of 4-N-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters

  摘要：

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

  DOI：

  10.1021/ol0518378

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.
• Hydrothermal Deamidation of 4-<i>N</i>-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters
  作者：Ireneusz Nowak、Morris J. Robins

  DOI：10.1021/ol0518378

  日期：2005.10.1

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.
• 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.