3'-deoxy-3'-thioinosine 3'-S-dimethylphosphorothiolate | 272785-88-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3'-deoxy-3'-thioinosine 3'-S-dimethylphosphorothiolate
• 英文别名: 9-[(2R,3S,4S,5R)-4-[dimethoxy(oxido)phosphaniumyl]sulfanyl-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 272785-88-3
• 化学式: C₁₂H₁₇N₄O₇PS
• 分子量: 392.329
• InChiKey: SRKVQNCOUIDNMW-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  176
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-thioinosine 3'-S-dimethylphosphorothiolate 在 氢气 作用下， 以 水 为溶剂， 生成 Phosphoric acid (2R,3S,4R,5R)-5-hydroxymethyl-4-mercapto-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester dimethyl ester 、 Thiophosphoric acid S-[(2R,3S,4S,5R)-4-hydroxy-2-hydroxymethyl-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester O-methyl ester 、 Phosphoric acid (2R,3S,4R,5R)-5-hydroxymethyl-4-mercapto-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester
  参考文献：
  名称：

  Preparation, Hydrolysis and Intramolecular Transesterification of 3′-Deoxy-3′-thioinosine 3′-S-Dimethylphosphorothiolate

  摘要：

  The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine 3'-S-phosphorothiolate have been followed over a wide aciditiy range by HPLC. At pH > 3, only hydroxide ion catalyzed isomerization to the 2'-dimethylphosphate takes place, whereas under more acidic conditions hydrolysis to the 2'-monomethylphosphate and 3'-S-monomethylphosphorothiolate competes. The latter is the only product accumulating in very acidic solutions (1 M hydrochloric acid). Mechanisms of the reactions are discussed.

  DOI：

  10.1080/15257770008035028
• 作为产物：
  描述：

  9-[(2R,3S,4S,5R)-3-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4-[(5-nitropyridin-2-yl)disulfanyl]oxolan-2-yl]-1H-purin-6-one 在 吡啶 、 盐酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.34h， 生成 3'-deoxy-3'-thioinosine 3'-S-dimethylphosphorothiolate
  参考文献：
  名称：

  Preparation, Hydrolysis and Intramolecular Transesterification of 3′-Deoxy-3′-thioinosine 3′-S-Dimethylphosphorothiolate

  摘要：

  The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine 3'-S-phosphorothiolate have been followed over a wide aciditiy range by HPLC. At pH > 3, only hydroxide ion catalyzed isomerization to the 2'-dimethylphosphate takes place, whereas under more acidic conditions hydrolysis to the 2'-monomethylphosphate and 3'-S-monomethylphosphorothiolate competes. The latter is the only product accumulating in very acidic solutions (1 M hydrochloric acid). Mechanisms of the reactions are discussed.

  DOI：

  10.1080/15257770008035028

文献信息

• Preparation, Hydrolysis and Intramolecular Transesterification of 3′-Deoxy-3′-thioinosine 3′-S-Dimethylphosphorothiolate
  作者：Mohamed I. Elzagheid、Esa Mäki、Ulla Kaukinen、Mikko Oivanen、Harri Lönnberg

  DOI：10.1080/15257770008035028

  日期：2000.4

  The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine 3'-S-phosphorothiolate have been followed over a wide aciditiy range by HPLC. At pH > 3, only hydroxide ion catalyzed isomerization to the 2'-dimethylphosphate takes place, whereas under more acidic conditions hydrolysis to the 2'-monomethylphosphate and 3'-S-monomethylphosphorothiolate competes. The latter is the only product accumulating in very acidic solutions (1 M hydrochloric acid). Mechanisms of the reactions are discussed.