(5S,6S,E)-methyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate | 1209778-27-7

• 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: (5S,6S,E)-methyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate
• CAS: 1209778-27-7
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: CAGPREOFHKCJQL-ITQKGHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5S,6S,E)-methyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate 在 甲醇 、 lithium hydroxide monohydrate 、 potassium hydrogensulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成 (5S,6S,E)-6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoic acid
  参考文献：
  名称：

  “Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

  摘要：

  An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated "click"-cyclization. Compared to cryptophycin-52, in vitro cytotoxicity of "clicktophycin-52" against the multidrug resistant human cancer cell line KB-V1 is only slightly reduced.

  DOI：

  10.1021/ol1000473
• 作为产物：
  描述：

  (2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol 、 丙烯酸甲酯（MA） 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以98%的产率得到(5S,6S,E)-methyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate
  参考文献：
  名称：

  “Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

  摘要：

  An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated "click"-cyclization. Compared to cryptophycin-52, in vitro cytotoxicity of "clicktophycin-52" against the multidrug resistant human cancer cell line KB-V1 is only slightly reduced.

  DOI：

  10.1021/ol1000473