3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-trifluoromethanesulfonyloxy-indole-1-carboxylic acid tert-butyl ester | 854443-86-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-trifluoromethanesulfonyloxy-indole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 3-[(2R)-3-methoxy-2-(methoxycarbonylamino)-3-oxopropyl]-6-(trifluoromethylsulfonyloxy)indole-1-carboxylate
• CAS: 854443-86-0
• 化学式: C₂₀H₂₃F₃N₂O₉S
• 分子量: 524.472
• InChiKey: XTTYOPATXFBHQE-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-trifluoromethanesulfonyloxy-indole-1-carboxylic acid tert-butyl ester 在 1,1'-双(二苯基膦)二茂铁 、 N-羟基-7-氮杂苯并三氮唑 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 碘代三甲硅烷 、 potassium acetate 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (R)-2-[2-(3,5-Dichloro-4-hydroxy-phenyl)-2-oxo-acetylamino]-3-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-3-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Isocomplestatin:  Total Synthesis and Stereochemical Revision

  摘要：

  A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product.

  DOI：

  10.1021/ja051790l
• 作为产物：
  描述：

  (2R,3aS,8aS)-8-Acetyl-6-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 在 4-二甲氨基吡啶 、 硫酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-trifluoromethanesulfonyloxy-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Isocomplestatin:  Total Synthesis and Stereochemical Revision

  摘要：

  A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product.

  DOI：

  10.1021/ja051790l