(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane | 151567-01-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane
• CAS: 151567-01-0
• 化学式: C₃₅H₄₈O₅SSi
• 分子量: 608.915
• InChiKey: AGQANWDHTKPKME-GMRCWXNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  42.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane 在 甲醇 、 二甲基硫 、 臭氧 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 Ethyl (3R,4R,5S)-2,2-difluoro-3-hydroxy-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(mesyloxy)-6-(benzyloxy)hexanoate
  参考文献：
  名称：

  Synthesis of a thromboxane A2 receptor antagonist possessing the dioxabicycloheptane nucleus of TXA2

  摘要：

  The synthesis of the TXA2/PGH2 receptor antagonist 6 from the known chiral intermediate (-)-8 is described. The critical reaction is the inversion of C-5 in 11a and 11b by an intramolecular cyclization reaction induced by nucleophilic reagents as shown in structure 13a. The key intermediate 22 was prepared in 26.5 % yield in five steps. Diastereoselectivity is high in all but one of the steps, the Reformatsky reaction, which leads to equal amounts of 11a and 11b. The design of 6 is based on the dioxabicycloheptane nucleus characteristic of TXA2 (1), which has been stabilized by fluorination. To this nucleus the two side chains are attached in cis orientation, and the omega-chain is modified as reported for the receptor antagonist (-)-5, which in turn is an analogue of PGH2 (3). These changes in the side chains have the effect of converting the powerful agonist 2 (DFTXA2) into a receptor antagonist devoid of agonist activity, which binds to the receptor with nanomolar affinity. These findings lend support to the view of a single TXA2/PGH2 receptor.

  DOI：

  10.1021/jo00073a035
• 作为产物：
  描述：

  甲基磺酰氯 、 (2S,3S)-1-<(tert-butyldiphenylsilyl)oxy>-2-(1-hexenyl)-3-hydroxy-4-(benzyloxy)butane 在 吡啶 作用下， 以90%的产率得到(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane
  参考文献：
  名称：

  Synthesis of a thromboxane A2 receptor antagonist possessing the dioxabicycloheptane nucleus of TXA2

  摘要：

  The synthesis of the TXA2/PGH2 receptor antagonist 6 from the known chiral intermediate (-)-8 is described. The critical reaction is the inversion of C-5 in 11a and 11b by an intramolecular cyclization reaction induced by nucleophilic reagents as shown in structure 13a. The key intermediate 22 was prepared in 26.5 % yield in five steps. Diastereoselectivity is high in all but one of the steps, the Reformatsky reaction, which leads to equal amounts of 11a and 11b. The design of 6 is based on the dioxabicycloheptane nucleus characteristic of TXA2 (1), which has been stabilized by fluorination. To this nucleus the two side chains are attached in cis orientation, and the omega-chain is modified as reported for the receptor antagonist (-)-5, which in turn is an analogue of PGH2 (3). These changes in the side chains have the effect of converting the powerful agonist 2 (DFTXA2) into a receptor antagonist devoid of agonist activity, which binds to the receptor with nanomolar affinity. These findings lend support to the view of a single TXA2/PGH2 receptor.

  DOI：

  10.1021/jo00073a035