(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one | 416843-12-4

• 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: (1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one
• 英文别名: (1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13'-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofutan-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
• CAS: 416843-12-4
• 化学式: C₄₅H₇₂O₇S
• 分子量: 757.128
• InChiKey: WCPPXZKEWNXTLG-CHQCGRFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.37
• 重原子数：
  53.0
• 可旋转键数：
  30.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one 在 Wilkinson's catalyst 氢气 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 25.34h， 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：

  (2R,5S,1'R,1''S)-2-(1'-methoxymethoxy-4'-pentynyl)-5-(1''-hydroxytridecyl)tetrahydrofuran 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 (1'''S,2''R,3RS,5S,5''S,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

  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.