(+/-)-methanesulfonic acid 4,4-bis-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enyl ester | 1193397-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (+/-)-methanesulfonic acid 4,4-bis-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enyl ester
• CAS: 1193397-08-8
• 化学式: C₂₀H₄₂O₅SSi₂
• 分子量: 450.787
• InChiKey: SSTAQIBOLBXFCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-methanesulfonic acid 4,4-bis-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enyl ester 、 丙二酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到(+/-)-2-[4,4-bis-(tert-butyldimethylsilanyloxymethyl)-cyclopent-2-enyl]malonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and Anti-Hiv Activity of 4′-Modified Cyclopentenyl PyrimidineC-Nucleosides

  摘要：

  Novel syntheses of 4-modified cyclopentenyl pyrimidine C-nucleosides were performed via C-C bond formation using S(N)2 alkylation via the key intermediate mesylates 6 and 16, which were prepared,from acyclic ketone derivatives. When antiviral evaluation of synthesized, compound was performed against various viruses such as HIV-1, HSV-1 and HSV-2, isocytidine analogue 20 showed, moderate anti-HIV activity in CEM cell line (EC50 = 13.1 mu mol).

  DOI：

  10.1080/15257770902946058
• 作为产物：
  描述：

  甲基磺酰氯 、 4,4-Bis[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(+/-)-methanesulfonic acid 4,4-bis-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enyl ester
  参考文献：
  名称：

  Synthesis and Anti-Hiv Activity of 4′-Modified Cyclopentenyl PyrimidineC-Nucleosides

  摘要：

  Novel syntheses of 4-modified cyclopentenyl pyrimidine C-nucleosides were performed via C-C bond formation using S(N)2 alkylation via the key intermediate mesylates 6 and 16, which were prepared,from acyclic ketone derivatives. When antiviral evaluation of synthesized, compound was performed against various viruses such as HIV-1, HSV-1 and HSV-2, isocytidine analogue 20 showed, moderate anti-HIV activity in CEM cell line (EC50 = 13.1 mu mol).

  DOI：

  10.1080/15257770902946058