(S)-1-((2R,3S,4S)-3-acetoxy-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidin-2-yl)-2-methyl-propyl benzoate | 1015841-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-((2R,3S,4S)-3-acetoxy-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidin-2-yl)-2-methyl-propyl benzoate
• 英文别名: [(1S)-1-[(2R,3S,4S)-3-acetyloxy-2-(hydroxymethyl)-4-methyl-5-oxopyrrolidin-2-yl]-2-methylpropyl] benzoate
• CAS: 1015841-33-4
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: IJMHIUDXYLDYDG-BMYCAMMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-((2R,3S,4S)-3-acetoxy-2-hydroxymethyl-4-methyl-5-oxo-pyrrolidin-2-yl)-2-methyl-propyl benzoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到
  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,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