Acetic acid (2R,3S,5R)-2-[(2-cyano-ethoxy)-(4-nitro-phenoxy)-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 379711-54-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: Acetic acid (2R,3S,5R)-2-[(2-cyano-ethoxy)-(4-nitro-phenoxy)-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 379711-54-3
• 化学式: C₂₁H₂₃N₄O₁₀P
• 分子量: 522.408
• InChiKey: AMKXFAJCDFCUEN-FFHMXWIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  185.01
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5R)-2-[(2-cyano-ethoxy)-(4-nitro-phenoxy)-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 dimethyl sulfide borane 、 氨 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  SYNTHESIS OF NEW CLASSES OF BORON-CONTAINING NUCLEOTIDES

  摘要：

  Four different types of boron-modified nucleotides are reported: P-boranophosphorothioates, P-cyanoboranophosphates, P-boranomethylphosphonates, and P3'-N5'-boranophosphoramidates. Synthesis of dinucleoside borano-phosphorothioates and nucleoside P-borano-P-thiomonophosphates via a lithium sulfide method is described. The Li2S method also provides an alternative way to synthesize phosphorothioates through a dinitrophenyl P(V) phosphotriester precursor. The mechanism of Li2S substitution was investigated.

  DOI：

  10.1081/ncn-100002335
• 作为产物：
  描述：

  对硝基苯酚 、 双(二异丙基氨基)(2-氰基乙氧基)膦 、 3'-O-acetylthymidine 在 四氮唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 Acetic acid (2R,3S,5R)-2-[(2-cyano-ethoxy)-(4-nitro-phenoxy)-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  SYNTHESIS OF NEW CLASSES OF BORON-CONTAINING NUCLEOTIDES

  摘要：

  Four different types of boron-modified nucleotides are reported: P-boranophosphorothioates, P-cyanoboranophosphates, P-boranomethylphosphonates, and P3'-N5'-boranophosphoramidates. Synthesis of dinucleoside borano-phosphorothioates and nucleoside P-borano-P-thiomonophosphates via a lithium sulfide method is described. The Li2S method also provides an alternative way to synthesize phosphorothioates through a dinitrophenyl P(V) phosphotriester precursor. The mechanism of Li2S substitution was investigated.

  DOI：

  10.1081/ncn-100002335