N⁴-isobutyryl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine | 153809-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N⁴-isobutyryl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine
• 英文别名: N-[1-[(6aR,8R,9R,9aS)-9-hydroxy-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: 153809-36-0
• 化学式: C₂₅H₄₅N₃O₇Si₂
• 分子量: 555.819
• InChiKey: ZBNZWVLTYPSGBA-VDEHWKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N⁴-isobutyryl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-cytidine 在 triethylamine tris(hydrogen fluoride) 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  胞苷 在 吡啶 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N⁴-isobutyryl-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

• 2′-<i>O</i>-Methyl Thiomethyl Modifications in Hammerhead Ribozymes
  作者：Alexander Karpeisky、Carolyn Gonzalez、Alex B. Burgin、Nassim Usman、Leonid Beigelman

  DOI：10.1080/07328319708006114

  日期：1997.7

  The synthesis of all four phosphoramidites of 2'-O-methylthiomethyl ribonucleosides and their incorporation into hammerhead ribozymes and influence on nuclease stability and catalytic activity is described.
• Building Blocks for Synthesis of Oligoarabinonucleotides: Preparation of Arabinonucleoside H-Phosphonates from Protected Ribonucleosides
  作者：Eriks Rozners、Erika Bizdena

  DOI：10.1080/15257779508010720

  日期：1995.11

  A straightforward and inexpensive synthesis of arabinonucleoside H-phosphonates has been developed. Arabinonucleosides were synthesised from protected ribonucleosides via 2'-keto derivatives. Reaction conditions have been optimised for compounds bearing labile N-protections. Further protecting group manipulation and phosphonylation gave the required H-phosphonate monomers.
• 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