(2R)-N-[(1R)-2-[[(1R)-2-(tert-butylamino)-1-(4-hydroxy-3-iodophenyl)-2-oxoethyl]amino]-1-(3,5-dichloro-4-hydroxyphenyl)-2-oxoethyl]-2-[[2-(3,5-dichloro-4-hydroxyphenyl)-2-oxoacetyl]amino]-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]propanamide | 854443-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R)-N-[(1R)-2-[[(1R)-2-(tert-butylamino)-1-(4-hydroxy-3-iodophenyl)-2-oxoethyl]amino]-1-(3,5-dichloro-4-hydroxyphenyl)-2-oxoethyl]-2-[[2-(3,5-dichloro-4-hydroxyphenyl)-2-oxoacetyl]amino]-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]propanamide
• CAS: 854443-91-7
• 化学式: C₄₅H₄₅BCl₄IN₅O₁₀
• 分子量: 1095.41
• InChiKey: ONBHPPKXIWLXAA-GJJQDPDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  66
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  228
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R)-N-[(1R)-2-[[(1R)-2-(tert-butylamino)-1-(4-hydroxy-3-iodophenyl)-2-oxoethyl]amino]-1-(3,5-dichloro-4-hydroxyphenyl)-2-oxoethyl]-2-[[2-(3,5-dichloro-4-hydroxyphenyl)-2-oxoacetyl]amino]-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]propanamide 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.25h， 生成
  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)-2-Amino-N-tert-butyl-2-(4-hydroxy-3-iodo-phenyl)-acetamide 在 盐酸 、 碳酸氢钠 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 (2R)-N-[(1R)-2-[[(1R)-2-(tert-butylamino)-1-(4-hydroxy-3-iodophenyl)-2-oxoethyl]amino]-1-(3,5-dichloro-4-hydroxyphenyl)-2-oxoethyl]-2-[[2-(3,5-dichloro-4-hydroxyphenyl)-2-oxoacetyl]amino]-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]propanamide
  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