(2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carboxylic acid | 1132754-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carboxylic acid
• CAS: 1132754-19-8
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: JHQPZYFRLIWIJX-YYQHBFALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carboxylic acid 在 (氯亚甲基)二甲基氯化铵 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 以67.9%的产率得到(4S,5S)-4-(hydroxymethyl)-5-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]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
• 作为产物：
  描述：

  methyl (2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.33h， 以95%的产率得到(2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carboxylic acid
  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