ethyl (E)-(6S)-(tert-butyldimethylsilyloxy)-henicosanoate | 891169-92-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-(6S)-(tert-butyldimethylsilyloxy)-henicosanoate
• CAS: 891169-92-9
• 化学式: C₂₉H₆₀O₃Si
• 分子量: 484.879
• InChiKey: SNJFPWGGAKHEIP-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.98
• 重原子数：
  33.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-(6S)-(tert-butyldimethylsilyloxy)-henicosanoate 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 生成 (6S)-(tert-butyldimethylsilyloxy)-henicosan-1-ol
  参考文献：
  名称：

  Antiparasite and antimycobacterial activity of passifloricin analogues

  摘要：

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.02.017
• 作为产物：
  描述：

  ethyl (E)-(6S)-(tert-butyldimethylsilyloxy)-henicos-2-enoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 ethyl (E)-(6S)-(tert-butyldimethylsilyloxy)-henicosanoate
  参考文献：
  名称：

  Antiparasite and antimycobacterial activity of passifloricin analogues

  摘要：

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.02.017