5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | 911218-28-5

• 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: 5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
• 英文别名: methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(1R,2S,3S,5S)-3-hydroxy-2-[(2R)-1-hydroxypropan-2-yl]-5-methylcyclopentyl]methoxy]-2-oxoethyl]-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• CAS: 911218-28-5
• 化学式: C₃₅H₅₀O₁₇
• 分子量: 742.772
• InChiKey: PBIYTGWLRJWJQQ-XMFKZVEZSA-N

物化性质

• 沸点：
  760.2±60.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  226
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 在 二乙胺 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以56%的产率得到5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Stereochemical Confirmation of the Secoiridoid Glucosides Nudiflosides D and A

  摘要：

  We describe herein an efficient access to the highly substituted cyclopentane unit present in the Nudifloside secoiridoid family via crotyl phosphonamide anion mediated conjugate addition to cyclopentenone.

  DOI：

  10.1021/ol0615230
• 作为产物：
  描述：

  木樨榄苷-11-甲酯 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.67h， 生成 5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Stereochemical Confirmation of the Secoiridoid Glucosides Nudiflosides D and A

  摘要：

  We describe herein an efficient access to the highly substituted cyclopentane unit present in the Nudifloside secoiridoid family via crotyl phosphonamide anion mediated conjugate addition to cyclopentenone.

  DOI：

  10.1021/ol0615230