(5R)-[(1R)-benzyloxy-13-[(5S)-methyl-2-oxo-3-phenylsulfanyltetrahydrofuran-3-yl]-tridec-2-enyl]-5H-furan-2-one

• 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: (5R)-[(1R)-benzyloxy-13-[(5S)-methyl-2-oxo-3-phenylsulfanyltetrahydrofuran-3-yl]-tridec-2-enyl]-5H-furan-2-one
• 英文别名: (5S)-5-methyl-3-[(E,13R)-13-[(2R)-5-oxo-2H-furan-2-yl]-13-phenylmethoxytridec-11-enyl]-3-phenylsulfanyloxolan-2-one
• 化学式: C₃₅H₄₄O₅S
• 分子量: 576.797
• InChiKey: CJUUEPQQWFAECI-BXSREMFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5R)-[(1R)-benzyloxy-13-[(5S)-methyl-2-oxo-3-phenylsulfanyltetrahydrofuran-3-yl]-tridec-2-enyl]-5H-furan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
  参考文献：
  名称：

  Convergent total synthesis of squamostolide

  摘要：

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.151
• 作为产物：
  描述：

  甘露醇 在 Hoveyda-Grubbs' first-generation catalyst 吡啶 、 乙酰溴 、 乙酸酐 、 四丁基碘化铵 、 二正丁基氧化锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 (5R)-[(1R)-benzyloxy-13-[(5S)-methyl-2-oxo-3-phenylsulfanyltetrahydrofuran-3-yl]-tridec-2-enyl]-5H-furan-2-one
  参考文献：
  名称：

  Convergent total synthesis of squamostolide

  摘要：

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.151

文献信息

• Convergent total synthesis of squamostolide
  作者：Kevin J. Quinn、Austin G. Smith、Carolyn M. Cammarano

  DOI：10.1016/j.tet.2007.03.151

  日期：2007.6

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.