(3S)-3-((1S)-hydroxy((1S,2R,3S,5S)-2-methyl-5-(prop-1-en-2-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)methyl)dihydrofuran-2(3H)-one | 1132754-26-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-3-((1S)-hydroxy((1S,2R,3S,5S)-2-methyl-5-(prop-1-en-2-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)methyl)dihydrofuran-2(3H)-one
• CAS: 1132754-26-7
• 化学式: C₁₉H₃₀O₅
• 分子量: 338.444
• InChiKey: MPYUXJOPNXGMKW-SVHYZOFNSA-N

物化性质

• 沸点：
  499.1±45.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-((1S)-hydroxy((1S,2R,3S,5S)-2-methyl-5-(prop-1-en-2-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)methyl)dihydrofuran-2(3H)-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以66.5%的产率得到
  参考文献：
  名称：

  Diastereoselective total synthesis of 8-epigrosheimin

  摘要：

  The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated gamma-butyrolactone ring. Our approach featured that the gamma-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative gamma-lactonization; and (3) an intramolecular aldehyde-ene cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.025
• 作为产物：
  描述：

  γ-丁内酯 、 (1S,2R,3S,5S)-2-methyl-5-(prop-1-en-2-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentane-1-carbaldehyde 在 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以72%的产率得到(3S)-3-((1S)-hydroxy((1S,2R,3S,5S)-2-methyl-5-(prop-1-en-2-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)methyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Diastereoselective total synthesis of 8-epigrosheimin

  摘要：

  The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated gamma-butyrolactone ring. Our approach featured that the gamma-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative gamma-lactonization; and (3) an intramolecular aldehyde-ene cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.025