Phosphoric acid allyl ester (2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-cyano-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 215318-33-5

• 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: Phosphoric acid allyl ester (2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-cyano-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS: 215318-33-5
• 化学式: C₂₃H₂₉N₆O₁₁P
• 分子量: 596.491
• InChiKey: QXLVNJGOSWXSNC-ZTSRVIJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  243.24
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid allyl ester (2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-cyano-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-d-arabino-pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation

  摘要：

  To investigate the stability of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentafuranosylcytosine 3'-phosphoric acid, its thymidine ester was prepared via the phosphoramidite method using allyl protection for the phosphate function. This ester is stable under acidic conditions but extremely labile under basic conditions, decomposing with a cleavage of the internucleotide bond even at pH 7.3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00459-4
• 作为产物：
  描述：

  3’-O-(4,4’-二甲氧基三苯甲基)胸苷 在 四氮唑 、 盐酸 、 叔丁基过氧化氢 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.13h， 生成 Phosphoric acid allyl ester (2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-cyano-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-d-arabino-pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation

  摘要：

  To investigate the stability of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentafuranosylcytosine 3'-phosphoric acid, its thymidine ester was prepared via the phosphoramidite method using allyl protection for the phosphate function. This ester is stable under acidic conditions but extremely labile under basic conditions, decomposing with a cleavage of the internucleotide bond even at pH 7.3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00459-4