(2R,5S,1'R,1''S)-2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran | 416843-09-9

• 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: (2R,5S,1'R,1''S)-2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran
• 英文别名: (2R,5S,1'R,1''S)-2-(1'-benzyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran
• CAS: 416843-09-9
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: ICFMUDKHUZOJDE-RRGQHJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  36.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,5S,1'R,1''S)-2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran 在 bis-triphenylphosphine-palladium(II) chloride 、 Wilkinson's catalyst sodium hydroxide 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 62.34h， 生成 (15R,16R,19S,20S,34S)-cis-solamin
  参考文献：
  名称：

  Total Synthesis of cis-Solamin

  摘要：

  [GRAPHICS]A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)(2)-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.

  DOI：

  10.1021/ol0102803
• 作为产物：
  描述：

  (Z,9S,10S)-10-(methoxymethoxy)docos-5-en-1-yn-9-ol 在 bis(acetylacetonate)oxovanadium 吡啶 、 叔丁基过氧化氢 、 4 A molecular sieve 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 17.0h， 生成 (2R,5S,1'R,1''S)-2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran
  参考文献：
  名称：

  Total Synthesis of cis-Solamin

  摘要：

  [GRAPHICS]A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)(2)-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.

  DOI：

  10.1021/ol0102803

文献信息

• Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I
  作者：Hidefumi Makabe、Yasunao Hattori、Yuka Kimura、Hiroyuki Konno、Masato Abe、Hideto Miyoshi、Akira Tanaka、Takayuki Oritani

  DOI：10.1016/j.tet.2004.09.011

  日期：2004.11

  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.