4-{2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-hydroxy-5-methylcyclopentylmethoxycarbonylmethyl}-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | 911218-27-4

• 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: 4-{2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-hydroxy-5-methylcyclopentylmethoxycarbonylmethyl}-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
• CAS: 911218-27-4
• 化学式: C₅₁H₆₈O₁₇Si
• 分子量: 981.176
• InChiKey: RHWRCYXESAFZKV-FNPYKWMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  69.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  214.95
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  4-{2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-hydroxy-5-methylcyclopentylmethoxycarbonylmethyl}-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到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
• 作为产物：
  描述：

  木樨榄苷-11-甲酯 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 4-{2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-hydroxy-5-methylcyclopentylmethoxycarbonylmethyl}-5-ethylidene-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