(1R,4S,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethenyl-7-oxabicyclo[4.1.0]heptan-2-one | 189942-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,4S,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethenyl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 189942-90-3
• 化学式: C₁₄H₂₄O₃Si
• 分子量: 268.428
• InChiKey: MMPRWIFPZWHQMI-LPTSXCQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethenyl-7-oxabicyclo[4.1.0]heptan-2-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 臭氧 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 (1S,2S,3R,5R,6R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-oxabicyclo[4.1.0]heptane-3-carbaldehyde
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Eutypoxide B

  摘要：

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.

  DOI：

  10.1021/jo9617326
• 作为产物：
  描述：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 sodium hydroxide 、 甲基锂 、 苄基三甲基氢氧化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 异辛烷 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 (1R,4S,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethenyl-7-oxabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Eutypoxide B

  摘要：

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.

  DOI：

  10.1021/jo9617326

文献信息

• Enantioselective Total Synthesis of (+)-Eutypoxide B
  作者：M. Teresa Barros、Christopher D. Maycock、M. Rita Ventura

  DOI：10.1021/jo9617326

  日期：1997.6.13

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.