(4S,5S)-4-Benzyloxycarbonylmethyl-5-{(S)-benzyloxy-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 365449-64-5

• 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: (4S,5S)-4-Benzyloxycarbonylmethyl-5-{(S)-benzyloxy-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 365449-64-5
• 化学式: C₄₂H₅₂N₂O₁₀
• 分子量: 744.882
• InChiKey: DTNWVNNBXUVYSW-QJZGYWKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  149.93
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Benzyloxycarbonylmethyl-5-{(S)-benzyloxy-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal Dowex 50-X₈ 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以75%的产率得到(3S,4S,5S)-3-氨基-4,5-二羟基-6-[[(1S)-1-[(3S)-8-羟基-1-氧代异色满-3-基]-3-甲基丁基]氨基]-6-氧代己酸
  参考文献：
  名称：

  Stereoselective Synthesis of Pseudopeptide Microbial Agent AI-77-B

  摘要：

  [GRAPHICS]An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.

  DOI：

  10.1021/ol0101279
• 作为产物：
  描述：

  (4S,5S)-4-Benzyloxycarbonylmethyl-5-{(S)-benzyloxy-[(S)-1-((S)-8-methoxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 magnesium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以93%的产率得到(4S,5S)-4-Benzyloxycarbonylmethyl-5-{(S)-benzyloxy-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Pseudopeptide Microbial Agent AI-77-B

  摘要：

  [GRAPHICS]An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.

  DOI：

  10.1021/ol0101279