9-[5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S-(O,O-dimethylphosphorothiolate)-2-O-(isopropydimethylsilyl)-β-D-ribofuranosyl]hypoxanthine | 272785-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9-[5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S-(O,O-dimethylphosphorothiolate)-2-O-(isopropydimethylsilyl)-β-D-ribofuranosyl]hypoxanthine
• CAS: 272785-87-2
• 化学式: C₃₇H₄₅N₄O₈PSSi
• 分子量: 764.912
• InChiKey: XUSWXHNFVUOXCR-QGGAYTEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  52.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136.02
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9-[5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S-(O,O-dimethylphosphorothiolate)-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
• 作为产物：
  描述：

  二甲基异丙基氯硅烷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 9-[5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S-(O,O-dimethylphosphorothiolate)-2-O-(isopropydimethylsilyl)-β-D-ribofuranosyl]hypoxanthine
  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