(E)-(4R,5R)-4-Benzyloxy-5-hydroxy-heptadec-2-enoic acid ethyl ester | 143812-41-3

• 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: (E)-(4R,5R)-4-Benzyloxy-5-hydroxy-heptadec-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4R,5R)-5-hydroxy-4-phenylmethoxyheptadec-2-enoate
• CAS: 143812-41-3
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: KWQWIOFVRZOADX-SSGBFYFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5R)-4-Benzyloxy-5-hydroxy-heptadec-2-enoic acid ethyl ester 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 27.0h， 生成 (5R)-5-[(1R)-1-羟基十三烷基]四氢呋喃-2-酮
  参考文献：
  名称：

  Syntheses and Cytotoxicities of Four Stereoisomers of Muricatacin from d -Glucose

  摘要：

  Four stereoisomers of muricatacin 1a-d were prepared by the reaction of corresponding aldehydes 4a-d, which in turn were prepared from D-glucose, with the anion of triethylphosphonoacetate followed by reduction and cyclization under acidic conditions. Cytotoxicities of four stereoisomers were tested against in vitro A-549 cell line as well as MCF-7 cell line. Stereochemistry at C-4 and C-5 position of muricatacin did not affect the cytotoxicities significantly. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00062-5
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-5-Dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 盐酸 、 sodium periodate 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 58.0h， 生成 (E)-(4R,5R)-4-Benzyloxy-5-hydroxy-heptadec-2-enoic acid ethyl ester
  参考文献：
  名称：

  Syntheses and Cytotoxicities of Four Stereoisomers of Muricatacin from d -Glucose

  摘要：

  Four stereoisomers of muricatacin 1a-d were prepared by the reaction of corresponding aldehydes 4a-d, which in turn were prepared from D-glucose, with the anion of triethylphosphonoacetate followed by reduction and cyclization under acidic conditions. Cytotoxicities of four stereoisomers were tested against in vitro A-549 cell line as well as MCF-7 cell line. Stereochemistry at C-4 and C-5 position of muricatacin did not affect the cytotoxicities significantly. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00062-5