Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester | 213455-82-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS: 213455-82-4
• 化学式: C₂₀H₃₅F₃O₆S
• 分子量: 460.556
• InChiKey: LZSVXLFWVQUWPY-XMTFNYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 在 盐酸 、 sodium tetrahydroborate 、 2-甲基-2-丁烯 、 草酰氯 、 dimethyl sulfide borane 、 双氧水 、 sodium hydride 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 140.33h， 生成 (2S,3R,4S,5S)-4-Benzyloxy-5-dodecyl-tetrahydro-furan-2,3-diol
  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：

  三氟甲磺酸酐 、 (3aR,5R,6S,6aR)-5-Dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-dodecyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl 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