(3S)-3-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]oxolan-2-one | 1132754-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S)-3-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]oxolan-2-one
• CAS: 1132754-12-1
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: KSTMSQHARNQDNZ-XDSHMYFISA-N

物化性质

• 沸点：
  432.1±35.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]oxolan-2-one 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.5h， 以66.7%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)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carbaldehyde 在 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以87%的产率得到(3S)-3-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]oxolan-2-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