(3S,4S,5R,6S)-6-isopropyl-3-methyl-2-oxo-8-phenyl-7,9-dioxa-1-azaspiro[4.5]dec-4-yl-acetate | 1015841-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3S,4S,5R,6S)-6-isopropyl-3-methyl-2-oxo-8-phenyl-7,9-dioxa-1-azaspiro[4.5]dec-4-yl-acetate
• CAS: 1015841-32-3
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: NIQIOXJBNSLXES-RTKIRCTNSA-N

物化性质

• 熔点：
  185-186 °C(Solvent: Chloroform)
• 沸点：
  518.0±50.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,6S)-6-isopropyl-3-methyl-2-oxo-8-phenyl-7,9-dioxa-1-azaspiro[4.5]dec-4-yl-acetate 在 DMDO 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以82%的产率得到(S)-1-((2R,3S,4S)-3-acetoxy-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidin-2-yl)-2-methyl-propyl benzoate
  参考文献：
  名称：

  Enantioselective Total Syntheses of Omuralide, 7-epi-Omuralide, and (+)-Lactacystin

  摘要：

  An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.

  DOI：

  10.1021/jo7027695
• 作为产物：
  描述：

  (3S,4S,5S,6S,8R)-4-hydroxy-6-isopropyl-3-methyl-8-phenyl-7,9-dioxa-1-azaspiro[4.5]decan-2-one 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以68%的产率得到(3S,4S,5R,6S)-6-isopropyl-3-methyl-2-oxo-8-phenyl-7,9-dioxa-1-azaspiro[4.5]dec-4-yl-acetate
  参考文献：
  名称：

  Enantioselective Total Syntheses of Omuralide, 7-epi-Omuralide, and (+)-Lactacystin

  摘要：

  An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.

  DOI：

  10.1021/jo7027695