4-(N-Isobutyryl)-3'-deoxycytidine | 159217-64-8

• 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: 4-(N-Isobutyryl)-3'-deoxycytidine
• 英文别名: N-[1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide
• CAS: 159217-64-8
• 化学式: C₁₃H₁₉N₃O₅
• 分子量: 297.311
• InChiKey: JUVCYVZSRLZVOX-YGOYTEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(N-Isobutyryl)-3'-deoxycytidine 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages

  摘要：

  Convenient, preparative scale synthetic routes to 2'-O-(beta-cyanoethyl N,N-diisopropylphosphoramidites) of 3'-deoxycytidine (1) and 3'-deoxyguanosine (2) are described. The 3'-deoxycytidine nucleoside 5 was constructed by a modified Hilbert-Johnson reaction in which N-(4-isobutyryl)-cytosine (4) was ribosylated with anomeric acetate 3. Nucleoside 5 was converted to 5'-O(dimethoxytrityl)-4-N-isobutyryl-3'-deoxycytidine (7) and phosphitylated to provide phosphoramidite 1. Access to derivatives of 3'-deoxyguanosine was provided by selective removal of the 3'-hydroxyl of guanosine (10). Thus, the 3'-O-thiocarbamate of 5'-O-(dimethoxytrityl)-2-N-(dimethylformamidyl)- 2'-O-(triisopropylsilyl)guanosine (12) was reduced with tributyltin hydride and converted to phosphoramidite 2. In results to be reported elsewhere, phosphoramidites 1 and 2 were used to prepare oligodeoxynucleotides containing novel 2',5'-phosphodiester linkages using automated solid-phase DNA synthesis methods with average stepwise coupling yields of >97%.

  DOI：

  10.1021/jo00103a014
• 作为产物：
  描述：

  2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine 在 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 4-(N-Isobutyryl)-3'-deoxycytidine
  参考文献：
  名称：

  Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages

  摘要：

  Convenient, preparative scale synthetic routes to 2'-O-(beta-cyanoethyl N,N-diisopropylphosphoramidites) of 3'-deoxycytidine (1) and 3'-deoxyguanosine (2) are described. The 3'-deoxycytidine nucleoside 5 was constructed by a modified Hilbert-Johnson reaction in which N-(4-isobutyryl)-cytosine (4) was ribosylated with anomeric acetate 3. Nucleoside 5 was converted to 5'-O(dimethoxytrityl)-4-N-isobutyryl-3'-deoxycytidine (7) and phosphitylated to provide phosphoramidite 1. Access to derivatives of 3'-deoxyguanosine was provided by selective removal of the 3'-hydroxyl of guanosine (10). Thus, the 3'-O-thiocarbamate of 5'-O-(dimethoxytrityl)-2-N-(dimethylformamidyl)- 2'-O-(triisopropylsilyl)guanosine (12) was reduced with tributyltin hydride and converted to phosphoramidite 2. In results to be reported elsewhere, phosphoramidites 1 and 2 were used to prepare oligodeoxynucleotides containing novel 2',5'-phosphodiester linkages using automated solid-phase DNA synthesis methods with average stepwise coupling yields of >97%.

  DOI：

  10.1021/jo00103a014

文献信息

• Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages
  作者：Terry L. Sheppard、Andrew T. Rosenblatt、Ronald Breslow

  DOI：10.1021/jo00103a014

  日期：1994.12

  Convenient, preparative scale synthetic routes to 2'-O-(beta-cyanoethyl N,N-diisopropylphosphoramidites) of 3'-deoxycytidine (1) and 3'-deoxyguanosine (2) are described. The 3'-deoxycytidine nucleoside 5 was constructed by a modified Hilbert-Johnson reaction in which N-(4-isobutyryl)-cytosine (4) was ribosylated with anomeric acetate 3. Nucleoside 5 was converted to 5'-O(dimethoxytrityl)-4-N-isobutyryl-3'-deoxycytidine (7) and phosphitylated to provide phosphoramidite 1. Access to derivatives of 3'-deoxyguanosine was provided by selective removal of the 3'-hydroxyl of guanosine (10). Thus, the 3'-O-thiocarbamate of 5'-O-(dimethoxytrityl)-2-N-(dimethylformamidyl)- 2'-O-(triisopropylsilyl)guanosine (12) was reduced with tributyltin hydride and converted to phosphoramidite 2. In results to be reported elsewhere, phosphoramidites 1 and 2 were used to prepare oligodeoxynucleotides containing novel 2',5'-phosphodiester linkages using automated solid-phase DNA synthesis methods with average stepwise coupling yields of >97%.