Thiophosphoric acid S-[(2R,3R,4S,5R)-2-hydroxymethyl-4-(isopropyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester O,O'-dimethyl ester | 272785-89-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: Thiophosphoric acid S-[(2R,3R,4S,5R)-2-hydroxymethyl-4-(isopropyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester O,O'-dimethyl ester
• CAS: 272785-89-4
• 化学式: C₁₇H₂₉N₄O₇PSSi
• 分子量: 492.565
• InChiKey: GCQJJELZFLJBKD-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  137.79
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Thiophosphoric acid S-[(2R,3R,4S,5R)-2-hydroxymethyl-4-(isopropyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester O,O'-dimethyl ester 在 盐酸 作用下， 反应 0.17h， 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
• 作为产物：
  描述：

  9-[5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S-(5-nitropyridyl-2-disulfanyl)-2-O-(isopropydimethylsilyl)-β-D-ribofuranosyl]hypoxanthine 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 Thiophosphoric acid S-[(2R,3R,4S,5R)-2-hydroxymethyl-4-(isopropyl-dimethyl-silanyloxy)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester O,O'-dimethyl 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