(4-Chloro-butyl)-methyl-phosphoramidic acid mono-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester | 501336-07-8

• 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: (4-Chloro-butyl)-methyl-phosphoramidic acid mono-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester
• 英文别名: N-(4-chlorobutyl)-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-N-methylphosphonamidic acid
• CAS: 501336-07-8
• 化学式: C₁₅H₂₅ClN₃O₇P
• 分子量: 425.806
• InChiKey: DGOFXHGNLHIYHR-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4-Chloro-butyl)-methyl-phosphoramidic acid mono-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 在 controlled pore glass 、 三乙胺 、 二氯乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 胸苷酸
  参考文献：
  名称：

  Novel Method for the Immobilization of Nucleotides

  摘要：

  A novel method for the immobilization of nucleotides has been developed. The strategy employs a highly reactive pyrrolidinium phosphoramidate zwitterion intermediate that undergoes nucleophilic attack by long-chain alkylamine-controlled pore glass (LCAA-CPG) to generate an immobilized nucleotide. Quantification of nucleotide loading was accomplished by acidic hydrolysis of the P-N bond and subsequent HPLC analysis of TMP in the presence of an internal standard. Typical nucleotide loadings of 51-59 mumol/g of support were observed.

  DOI：

  10.1021/ol0273607
• 作为产物：
  描述：

  5'-thymidyl benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (4-Chloro-butyl)-methyl-phosphoramidic acid mono-[(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：

  Novel Method for the Immobilization of Nucleotides

  摘要：

  A novel method for the immobilization of nucleotides has been developed. The strategy employs a highly reactive pyrrolidinium phosphoramidate zwitterion intermediate that undergoes nucleophilic attack by long-chain alkylamine-controlled pore glass (LCAA-CPG) to generate an immobilized nucleotide. Quantification of nucleotide loading was accomplished by acidic hydrolysis of the P-N bond and subsequent HPLC analysis of TMP in the presence of an internal standard. Typical nucleotide loadings of 51-59 mumol/g of support were observed.

  DOI：

  10.1021/ol0273607

文献信息

• Novel Method for the Immobilization of Nucleotides
  作者：Caren L. Freel Meyers、Richard F. Borch

  DOI：10.1021/ol0273607

  日期：2003.2.1

  A novel method for the immobilization of nucleotides has been developed. The strategy employs a highly reactive pyrrolidinium phosphoramidate zwitterion intermediate that undergoes nucleophilic attack by long-chain alkylamine-controlled pore glass (LCAA-CPG) to generate an immobilized nucleotide. Quantification of nucleotide loading was accomplished by acidic hydrolysis of the P-N bond and subsequent HPLC analysis of TMP in the presence of an internal standard. Typical nucleotide loadings of 51-59 mumol/g of support were observed.