(3RS,5S,2'S,6'R,13'R,14'R,17'R,18'R)-[13',18'-di-(t-butyldimethylsilyloxy)-2',6':14',17'-dioxido-8'-oxo-triacontanyl]-5-methyl-3-(phenylthio)tetrahydrofuran-2-one | 1064038-95-4

• 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: (3RS,5S,2'S,6'R,13'R,14'R,17'R,18'R)-[13',18'-di-(t-butyldimethylsilyloxy)-2',6':14',17'-dioxido-8'-oxo-triacontanyl]-5-methyl-3-(phenylthio)tetrahydrofuran-2-one
• CAS: 1064038-95-4
• 化学式: C₅₃H₉₄O₇SSi₂
• 分子量: 931.562
• InChiKey: GBXKOEQMIVFZTM-DMGLYYHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.34
• 重原子数：
  63.0
• 可旋转键数：
  28.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3RS,5S,2'S,6'R,13'R,14'R,17'R,18'R)-[13',18'-di-(t-butyldimethylsilyloxy)-2',6':14',17'-dioxido-8'-oxo-triacontanyl]-5-methyl-3-(phenylthio)tetrahydrofuran-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Structural Determination of Montanacin D by Total Synthesis

  摘要：

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.

  DOI：

  10.1021/ol801576z
• 作为产物：
  描述：

  (3RS,5S,2'S,6'R,13'R,14'R,17'R,18'R)-[13',18'-di-(t-butyldimethylsilyloxy)-2',6':14',17'-dioxido-8'-oxo-9'-triacontenyl]-5-methyl-3-(phenylthio)tetrahydrofuran-2-one 在 platinum(IV) oxide 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以81%的产率得到(3RS,5S,2'S,6'R,13'R,14'R,17'R,18'R)-[13',18'-di-(t-butyldimethylsilyloxy)-2',6':14',17'-dioxido-8'-oxo-triacontanyl]-5-methyl-3-(phenylthio)tetrahydrofuran-2-one
  参考文献：
  名称：

  Structural Determination of Montanacin D by Total Synthesis

  摘要：

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.

  DOI：

  10.1021/ol801576z