Pentanedioic acid allyl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 178111-64-3

• 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: Pentanedioic acid allyl 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: 178111-64-3
• 化学式: C₁₈H₂₄N₂O₈
• 分子量: 396.397
• InChiKey: RSGMIOYVNQVEKQ-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  136.92
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Pentanedioic acid allyl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 生成
  参考文献：
  名称：

  Synthesis of a nucleoside hapten with a [P(O)-O-N] linkage to elicit catalytic antibodies with phosphodiesterase activity

  摘要：

  The nucleoside analogue 1 incorporating a [P(O)-O-N] linkage was synthesized as a hapten to obtain catalytic antibodies that may cleave a phosphodiester bond. Secondary alcohol 15 was successfully phosphorylated with the phosphodiester derived from hydroxylamine derivative 7b to give a protected form of the hapten. Deprotection was accomplished using Pd-catalyzed deallylation that afforded hapten 1 after HPLC purification. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00169-2
• 作为产物：
  描述：

  Pentanedioic acid allyl ester (2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到Pentanedioic acid allyl 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：

  Synthesis of a nucleoside hapten with a [P(O)-O-N] linkage to elicit catalytic antibodies with phosphodiesterase activity

  摘要：

  The nucleoside analogue 1 incorporating a [P(O)-O-N] linkage was synthesized as a hapten to obtain catalytic antibodies that may cleave a phosphodiester bond. Secondary alcohol 15 was successfully phosphorylated with the phosphodiester derived from hydroxylamine derivative 7b to give a protected form of the hapten. Deprotection was accomplished using Pd-catalyzed deallylation that afforded hapten 1 after HPLC purification. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00169-2