(4S,5R,6S)-5-Acetyl-4-(2-oxo-ethyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | 30657-86-4

• 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: (4S,5R,6S)-5-Acetyl-4-(2-oxo-ethyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
• CAS: 30657-86-4
• 化学式: C₂₅H₃₂O₁₅
• 分子量: 572.52
• InChiKey: ONVJUVKPOKIVJN-IFULQXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.09
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  193.33
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-5-Acetyl-4-(2-oxo-ethyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 jones' reagent 作用下， 以 1,4-二氧六环 、 乙醚 、 丙酮 为溶剂， 反应 1.83h， 生成 8-epikingiside acetate
  参考文献：
  名称：

  Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors

  摘要：

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.

  DOI：

  10.1016/0031-9422(95)00211-o
• 作为产物：
  描述：

  (1S,4aS,7aS)-6,7-Dihydroxy-7-methyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 在 sodium periodate 、 水 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以32%的产率得到(4S,5R,6S)-5-Acetyl-4-(2-oxo-ethyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors

  摘要：

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.

  DOI：

  10.1016/0031-9422(95)00211-o