3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester | 854443-87-1

• 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-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 3-[(2R)-3-methoxy-2-(methoxycarbonylamino)-3-oxopropyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate
• CAS: 854443-87-1
• 化学式: C₂₅H₃₅BN₂O₈
• 分子量: 502.372
• InChiKey: RODFCOIZQREUIE-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester 在 N-羟基-7-氮杂苯并三氮唑 、 碘代三甲硅烷 、 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 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 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：

  (R)-3-(6-Hydroxy-1H-indol-3-yl)-2-methoxycarbonylamino-propionic acid methyl ester 在 4-二甲氨基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-((R)-2-Methoxycarbonyl-2-methoxycarbonylamino-ethyl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-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

文献信息

• Isocomplestatin:  Total Synthesis and Stereochemical Revision
  作者：Toshio Shinohara、Hongbo Deng、Marc L. Snapper、Amir H. Hoveyda

  DOI：10.1021/ja051790l

  日期：2005.5.25

  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.