(1S,3S,5S)-1-{[(1R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl}-8-oxabicyclo[3.2.1]oct-6-en-3-yl acetate | 863912-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,5S)-1-{[(1R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl}-8-oxabicyclo[3.2.1]oct-6-en-3-yl acetate
• CAS: 863912-51-0
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: PWHBTBVPVAVKOE-VRXFMZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (1S,3S,5S)-1-{[(1R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl}-8-oxabicyclo[3.2.1]oct-6-en-3-yl acetate 在 吡啶 、 4-二甲氨基吡啶 、 三氯化硼 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 51.5h， 生成 (1S,6S)-4-({(4R,6R)-4,6-bis[(4-methoxybenzoyl)oxy]cyclohept-1-en-1-yl}methyl)-6-[(2,2-dimethylpropanoyl)oxy]cyclohept-3-en-1-yl 4-methoxybenzoate
  参考文献：
  名称：

  Enzymatic desymmetrization of 1,1′-methylenedi[(1R,1′S,3R,3′S,5S,5′R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-ene-1-yl]: novel precursors of long chain polyketides

  摘要：

  meso-1,1'-Methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-S-oxabicyclo[3.2.1]oct-6-ene-1-yl] 14 obtained through the [4+3]-cycloaddition of 2,T-methylenedifuran to oxyallyl cation, followed by reduction, has been desymmetrized by means of a lipase catalyzed transesterification to afford (1 S,3S,5S)-1-{[(1 R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2. 1]oct-6-en-yl]methyl)-8-oxabicyclo[3.2.1]loct-6-en-3-yl acetate (-)-15 (89% ee). This compound was transformed into aromatic ester derivatives for establishing the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.038
• 作为产物：
  描述：

  meso-1,1'-methylenedi[(1R,1'S,5S,5'R)-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl] 在 Candida cylindracea 、 potassium tri-sec-butyl-borohydride 作用下， 反应 10.0h， 生成 (1S,3S,5S)-1-{[(1R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl}-8-oxabicyclo[3.2.1]oct-6-en-3-yl acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of 1,1′-methylenedi[(1R,1′S,3R,3′S,5S,5′R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-ene-1-yl]: novel precursors of long chain polyketides

  摘要：

  meso-1,1'-Methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-S-oxabicyclo[3.2.1]oct-6-ene-1-yl] 14 obtained through the [4+3]-cycloaddition of 2,T-methylenedifuran to oxyallyl cation, followed by reduction, has been desymmetrized by means of a lipase catalyzed transesterification to afford (1 S,3S,5S)-1-{[(1 R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2. 1]oct-6-en-yl]methyl)-8-oxabicyclo[3.2.1]loct-6-en-3-yl acetate (-)-15 (89% ee). This compound was transformed into aromatic ester derivatives for establishing the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.038