methyl (2R)-4-hydroxy-2-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]butanoate | 1132754-17-6

• 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: methyl (2R)-4-hydroxy-2-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]butanoate
• CAS: 1132754-17-6
• 化学式: C₁₇H₃₀O₆
• 分子量: 330.422
• InChiKey: RMVWYQWHUCIQIE-RCZWDNKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R)-4-hydroxy-2-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]butanoate 在 2,2,6,6-四甲基哌啶氧化物 、 3,3-二甲基丁酰氯 、 碳酸氢钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 以89%的产率得到methyl (2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carboxylate
  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：

  重氮甲烷 、 (3R)-3-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]oxolan-2-one 在 氢氧化钾 、 盐酸 作用下， 以 四氢呋喃 、 水 、 乙醚 为溶剂， 反应 4.33h， 以94%的产率得到methyl (2R)-4-hydroxy-2-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]butanoate
  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

文献信息

• Diastereoselective total synthesis of 8-epigrosheimin
  作者：Haishen Yang、Xiaoxiao Qiao、Fangyi Li、Hui Ma、Longguan Xie、Xiaohua Xu

  DOI：10.1016/j.tetlet.2008.12.025

  日期：2009.3

  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.