N⁴-isobutyryl-2'-O-methyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine | 153809-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N⁴-isobutyryl-2'-O-methyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine
• 英文别名: N-[1-[(6aR,8R,9R,9aR)-9-methoxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide
• CAS: 153809-37-1
• 化学式: C₂₆H₄₇N₃O₇Si₂
• 分子量: 569.846
• InChiKey: IQOUUPBIYLIHEP-HBAHCVPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N⁴-isobutyryl-2'-O-methyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine 在 吡啶 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 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 、 三乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 N⁴-isobutyryl-2'-O-methyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine
  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