N⁴-isobutyryl-2'-O-methylcytidine | 153809-38-2

• 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: N⁴-isobutyryl-2'-O-methylcytidine
• 英文别名: N-[1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide
• CAS: 153809-38-2
• 化学式: C₁₄H₂₁N₃O₆
• 分子量: 327.337
• InChiKey: MSWAVGPJPWPQGJ-UORFTKCHSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁴-isobutyryl-2'-O-methylcytidine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyryl-2'-O-methylcytidine-3'-(methyl-N,N-diisopropylphosphonamidite)
  参考文献：
  名称：

  A Convenient High Yield Synthesis of N⁴-Isobutyryl-2′-O-Methylcytidine and Its Monomer Units For Incorporation into Oligonucleotides

  摘要：

  We designed an efficient three step procedure for the synthesis of N-4-isobutyryl-2'-O-methylcytidine. This protected nucleoside was then used to prepare a methylphosphonamidite monomer for incorporation into oligonucleotides. Transamination at the C-4 position of cytidine using ethylenediamine, which has been reported for the N-4-benzoyl cytidine, was not observed with N-4-isobutyryl protected 2'-O-methylcytidine

  DOI：

  10.1080/07328319308016200
• 作为产物：
  描述：

  胞苷 在 吡啶 、 水 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 N⁴-isobutyryl-2'-O-methylcytidine
  参考文献：
  名称：

  A Convenient High Yield Synthesis of N⁴-Isobutyryl-2′-O-Methylcytidine and Its Monomer Units For Incorporation into Oligonucleotides

  摘要：

  We designed an efficient three step procedure for the synthesis of N-4-isobutyryl-2'-O-methylcytidine. This protected nucleoside was then used to prepare a methylphosphonamidite monomer for incorporation into oligonucleotides. Transamination at the C-4 position of cytidine using ethylenediamine, which has been reported for the N-4-benzoyl cytidine, was not observed with N-4-isobutyryl protected 2'-O-methylcytidine

  DOI：

  10.1080/07328319308016200

文献信息

• A Convenient High Yield Synthesis of N⁴-Isobutyryl-2′-O-Methylcytidine and Its Monomer Units For Incorporation into Oligonucleotides
  作者：Morteza M. Vaghefi、Richard I. Hogrefe

  DOI：10.1080/07328319308016200

  日期：1993.12

  We designed an efficient three step procedure for the synthesis of N-4-isobutyryl-2'-O-methylcytidine. This protected nucleoside was then used to prepare a methylphosphonamidite monomer for incorporation into oligonucleotides. Transamination at the C-4 position of cytidine using ethylenediamine, which has been reported for the N-4-benzoyl cytidine, was not observed with N-4-isobutyryl protected 2'-O-methylcytidine