(S)-3-(1-Benzenesulfonyl-5-benzenesulfonyloxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester | 150804-44-7

• 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)-3-(1-Benzenesulfonyl-5-benzenesulfonyloxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester
• 英文别名: methyl (2S)-3-[1-(benzenesulfonyl)-5-(benzenesulfonyloxy)indol-3-yl]-2-(methoxycarbonylamino)-2-methylpropanoate
• CAS: 150804-44-7
• 化学式: C₂₇H₂₆N₂O₉S₂
• 分子量: 586.643
• InChiKey: JERVKGVZWITONJ-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-3-(1-Benzenesulfonyl-5-benzenesulfonyloxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester 在 氢氧化钾 、 三(2-氯乙基)胺 、 sodium 作用下， 反应 130.0h， 生成 α-methyl-5-hydroxytryptophan
  参考文献：
  名称：

  Asymmetric Synthesis of a-Substituted 5-Hydroxytryptophan Derivatives

  摘要：

  5-hydroxytryptophan was converted to pyrroloindole (3), which on deprotonation with LDA and subsequent reaction with alkyl halides gave the C-2 alkylated derivatives (6-9) cleanly with retention of configuration. Reversion to the 5-hydroxytryptophan skeleton was then achieved by stirring in trifluoroacetic acid and deprotection by treatment with sodium in liquid ammonia followed by saponification.

  DOI：

  10.3987/com-92-6313
• 作为产物：
  描述：

  (2S,3aR,8aS)-8-Benzenesulfonyl-5-benzenesulfonyloxy-2-methyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 在 三氟乙酸 作用下， 以95%的产率得到(S)-3-(1-Benzenesulfonyl-5-benzenesulfonyloxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of a-Substituted 5-Hydroxytryptophan Derivatives

  摘要：

  5-hydroxytryptophan was converted to pyrroloindole (3), which on deprotonation with LDA and subsequent reaction with alkyl halides gave the C-2 alkylated derivatives (6-9) cleanly with retention of configuration. Reversion to the 5-hydroxytryptophan skeleton was then achieved by stirring in trifluoroacetic acid and deprotection by treatment with sodium in liquid ammonia followed by saponification.

  DOI：

  10.3987/com-92-6313