[(2R,3S,5S)-5-(2,6-diaminopurin-9-yl)-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate | 234092-41-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: [(2R,3S,5S)-5-(2,6-diaminopurin-9-yl)-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate
• CAS: 234092-41-2
• 化学式: C₂₆H₂₆N₆O₄S
• 分子量: 518.596
• InChiKey: JBMQQCBLWQRWSI-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  174
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5S)-5-(2,6-diaminopurin-9-yl)-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate 在 sodium methylate 、 adenosine deaminase 作用下， 以 甲醇 为溶剂， 反应 342.0h， 生成 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-2-amino-1,6-dihydro-6-oxopurine
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides

  摘要：

  Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9 alpha and 9 beta anomers as major products. These anomers were separated and converted to 2'-deoxy-4'-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their alpha-anomers.

  DOI：

  10.1080/15257779908041540
• 作为产物：
  描述：

  9-Trimethylsilyl-2,6-dichlorpurin 在 sodium azide 、 三氟甲磺酸三甲基硅酯 、 四氯化锡 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 [(2R,3S,5S)-5-(2,6-diaminopurin-9-yl)-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides

  摘要：

  Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9 alpha and 9 beta anomers as major products. These anomers were separated and converted to 2'-deoxy-4'-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their alpha-anomers.

  DOI：

  10.1080/15257779908041540

文献信息

• Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides
  作者：Lea Messini、Kamal N. Tiwari、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257779908041540

  日期：1999.4

  Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9 alpha and 9 beta anomers as major products. These anomers were separated and converted to 2'-deoxy-4'-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their alpha-anomers.