(3aR,5S,6R,6aR)-6-Benzyloxy-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole | 213455-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,5S,6R,6aR)-6-Benzyloxy-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS: 213455-87-9
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: KAWQWJIBJHTXEW-ZYQDXHPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  30.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6R,6aR)-6-Benzyloxy-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 在 palladium on activated charcoal 盐酸 、 sodium periodate 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙酸乙酯 为溶剂， 反应 76.5h， 生成 (4S,5S)-4-Benzyloxy-5-hydroxy-heptadecanoic 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
• 作为产物：
  描述：

  (3aR,5S,6S,6aR)-5-Dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 sodium tetrahydroborate 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 20.33h， 生成 (3aR,5S,6R,6aR)-6-Benzyloxy-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
  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