4-((4S,5S)-5-(2-((4S,5S)-2,2-dimethyl-5-((Z)-tetradec-3-enyl)-1,3-dioxolan-4-yl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,2-diyl diacetate | 1186497-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((4S,5S)-5-(2-((4S,5S)-2,2-dimethyl-5-((Z)-tetradec-3-enyl)-1,3-dioxolan-4-yl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,2-diyl diacetate
• 英文别名: [2-acetyloxy-4-[(4S,5S)-5-[2-[(4S,5S)-2,2-dimethyl-5-[(Z)-tetradec-3-enyl]-1,3-dioxolan-4-yl]ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]butyl] acetate
• CAS: 1186497-49-3
• 化学式: C₃₄H₆₀O₈
• 分子量: 596.846
• InChiKey: MSUPOSMSMPDWMV-CVWPIZAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  42
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-((4S,5S)-5-(2-((4S,5S)-2,2-dimethyl-5-((Z)-tetradec-3-enyl)-1,3-dioxolan-4-yl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,2-diyl diacetate 在 potassium carbonate 、 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以89%的产率得到3-((4S,5S)-5-(2-((4S,5S)-2,2-dimethyl-5-((Z)-tetradec-3-enyl)-1,3-dioxolan-4-yl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanal
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959
• 作为产物：
  描述：

  4-((4S,5S)-5-(2-((4S,5S)-2,2-dimethyl-5-(3-oxopropyl)-1,3-dioxolan-4-yl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,2-diyl diacetate 、 (1-十一烷基)三苯基鏻溴化物 在 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 反应 16.33h， 以100%的产率得到4-((4S,5S)-5-(2-((4S,5S)-2,2-dimethyl-5-((Z)-tetradec-3-enyl)-1,3-dioxolan-4-yl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,2-diyl diacetate
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959