2',3',5'-tri-O-benzoylcytidine 4-N-(O,O-bis(2-cyanoethyl) phosphoramidate) | 154971-71-8

• 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: 2',3',5'-tri-O-benzoylcytidine 4-N-(O,O-bis(2-cyanoethyl) phosphoramidate)
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[4-[bis(2-cyanoethoxy)phosphorylamino]-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl benzoate
• CAS: 154971-71-8
• 化学式: C₃₆H₃₂N₅O₁₁P
• 分子量: 741.651
• InChiKey: JFNJYALAYPLIKR-PYTKSMOKSA-N

物化性质

• 沸点：
  874.8±75.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  216
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-benzoylcytidine 4-N-(O,O-bis(2-cyanoethyl) phosphoramidate) 生成 [1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-phosphoramidic acid
  参考文献：
  名称：

  New Strategies for the Chemical Synthesis of Biologically Important Nucleic Acid Derivatives

  摘要：

  This paper describes general methods for the synthesis of N-phosphorylated ribonucleosides and oligonucleotides containing a 2'-O-phosphorylated or 2'-O-thiophosphorylated ribonucleoside. The NMR-based conformational analysis and computational molecular dynamics simulation of the 2'-O-phosphorylated ribonucleoside residue in such modified oligonucleotides suggested that the ribose residue existed preferentially in a C2'-endo conformation, it was also found that simple heating of 2'-O-phosphorylated oligonucleotides resulted in rapid dethiophosphorylation.

  DOI：

  10.1080/07328319808004744
• 作为产物：
  描述：

  双(2-氰乙基)-N,N-二异丙基亚磷酰胺 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2',3',5'-tri-O-benzoylcytidine 4-N-(O,O-bis(2-cyanoethyl) phosphoramidate)
  参考文献：
  名称：

  New Strategies for the Chemical Synthesis of Biologically Important Nucleic Acid Derivatives

  摘要：

  This paper describes general methods for the synthesis of N-phosphorylated ribonucleosides and oligonucleotides containing a 2'-O-phosphorylated or 2'-O-thiophosphorylated ribonucleoside. The NMR-based conformational analysis and computational molecular dynamics simulation of the 2'-O-phosphorylated ribonucleoside residue in such modified oligonucleotides suggested that the ribose residue existed preferentially in a C2'-endo conformation, it was also found that simple heating of 2'-O-phosphorylated oligonucleotides resulted in rapid dethiophosphorylation.

  DOI：

  10.1080/07328319808004744

文献信息

• Synthesis and Properties of N-Phosphorylated Ribonucleosides
  作者：Takeshi Wada、Tomohisa Moriguchi、Mitsuo Sekine

  DOI：10.1021/ja00101a011

  日期：1994.11

  A new class of phosphorylated nucleosides, i.e., adenosine 6-N-phosphoramidate (6-N-AMP) and related derivatives, were synthesized in good yields via phosphitylation of the amino group of appropriately protected adenosine derivatives. In a similar manner, cytidine 4-N-phosphoramidate (4-N-CMP), guanosine 2-N-phosphoramidate (2-N-GMP), and their diethyl ester derivatives were synthesized. These new compounds were characterized by H-1, C-13, and P-31 NMR, UV, CD, IR, electrophoresis, and mass spectroscopy. The physical and chemical properties of these N-phosphorylated ribonucleoside derivatives have been studied in detail.
• New Strategies for the Chemical Synthesis of Biologically Important Nucleic Acid Derivatives
  作者：Mitsuo. Sekine、Hiroyuki. Tsuruoka、Koh-ichiro. Shohda、Tomohisa. Moriguchi、Tomohisa. Wada

  DOI：10.1080/07328319808004744

  日期：1998.9

  This paper describes general methods for the synthesis of N-phosphorylated ribonucleosides and oligonucleotides containing a 2'-O-phosphorylated or 2'-O-thiophosphorylated ribonucleoside. The NMR-based conformational analysis and computational molecular dynamics simulation of the 2'-O-phosphorylated ribonucleoside residue in such modified oligonucleotides suggested that the ribose residue existed preferentially in a C2'-endo conformation, it was also found that simple heating of 2'-O-phosphorylated oligonucleotides resulted in rapid dethiophosphorylation.