(3S,4S)-3-hexyl-4-((R)-2-hydroxytridec-5-enyl)-oxetan-2-one

• 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: (3S,4S)-3-hexyl-4-((R)-2-hydroxytridec-5-enyl)-oxetan-2-one
• 英文别名: (2R,3S,4S)-3-hexyl-4-(2-hydroxy-tridec-5-enyl)-oxetan-2-one；(3S,4S)-3-hexyl-4-[(2R)-2-hydroxytridec-5-enyl]oxetan-2-one
• 化学式: C₂₂H₄₀O₃
• 分子量: 352.558
• InChiKey: FRSRRPYDOYLOGF-HKBOAZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-hexyl-4-((R)-2-hydroxytridec-5-enyl)-oxetan-2-one 在 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 奥利司他
  参考文献：
  名称：

  Total Synthesis and Comparative Analysis of Orlistat, Valilactone, and a Transposed Orlistat Derivative:  Inhibitors of Fatty Acid Synthase

  摘要：

  Concise syntheses of orlistat ( Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.

  DOI：

  10.1021/ol061651o

文献信息

• BETA-LACTONE COMPOUNDS
  申请人：Smith Jeffrey W.

  公开号：US20090124681A1

  公开（公告）日：2009-05-14

  The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R 1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.

  本发明提供具有一般结构A的化合物，或其药学上可接受的衍生物：其中R是烷基基团，R1包括至少一种从烷基、烯基、芳基、杂环、羟基、酯、酰胺、醛基和卤素组成的基团。
• Total Synthesis and Comparative Analysis of Orlistat, Valilactone, and a Transposed Orlistat Derivative:  Inhibitors of Fatty Acid Synthase
  作者：Gil Ma、Manuel Zancanella、Yatsandra Oyola、Robyn D. Richardson、Jeffrey W. Smith、Daniel Romo

  DOI：10.1021/ol061651o

  日期：2006.9.1

  Concise syntheses of orlistat ( Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.