(2R,5S,1'R,1''S)-2-(1'-hydroxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran | 416843-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,5S,1'R,1''S)-2-(1'-hydroxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran
• 英文别名: (1R)-1-[(2R,5S)-5-[(1S)-1-(methoxymethoxy)tridecyl]oxolan-2-yl]pent-4-yn-1-ol
• CAS: 416843-08-8
• 化学式: C₂₄H₄₄O₄
• 分子量: 396.611
• InChiKey: XTNWQPSHUONZET-LWSSLDFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,5S,1'R,1''S)-2-(1'-hydroxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 (1'''S,2''R,3RS,5S,5''S,7'Z,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I

  摘要：

  A convergent total synthesis of cis-solamin (1a) and its diastereomer (1b) was accomplished. A key reaction of this approach was the use of VO(acac)(2)-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol 3 followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a. Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.011
• 作为产物：
  描述：

  (2R,5S,1'R,1''S)-2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以92%的产率得到(2R,5S,1'R,1''S)-2-(1'-hydroxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran
  参考文献：
  名称：

  Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I

  摘要：

  A convergent total synthesis of cis-solamin (1a) and its diastereomer (1b) was accomplished. A key reaction of this approach was the use of VO(acac)(2)-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol 3 followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a. Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.011