methyl (2R)-2-[[(8R,11R,14S)-8-[[(2R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetyl]amino]-11-(3,5-dichloro-4-hydroxyphenyl)-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carbonyl]amino]-2-(4-hydroxyphenyl)acetate | 586413-73-2

• 英文名称: methyl (2R)-2-[[(8R,11R,14S)-8-[[(2R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetyl]amino]-11-(3,5-dichloro-4-hydroxyphenyl)-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carbonyl]amino]-2-(4-hydroxyphenyl)acetate
• CAS: 586413-73-2
• 化学式: C₄₃H₃₆Cl₄IN₅O₁₁
• 分子量: 1067.5
• InChiKey: VNQIJVATHUUTSK-ALERHIRMSA-N

物化性质

• 沸点：
  1139.9±65.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  64
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  250
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R)-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]propanoic acid 、 methyl (2R)-2-[[(8R,11R,14S)-8-[[(2R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetyl]amino]-11-(3,5-dichloro-4-hydroxyphenyl)-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carbonyl]amino]-2-(4-hydroxyphenyl)acetate 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到methyl (2R)-2-[[(8R,11R,14S)-11-(3,5-dichloro-4-hydroxyphenyl)-8-[[(2R)-2-(3,5-dichloro-4-hydroxyphenyl)-2-[[(2R)-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]propanoyl]amino]acetyl]amino]-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carbonyl]amino]-2-(4-hydroxyphenyl)acetate
  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：

  methyl (2R)-2-[[(8R,11R,14S)-11-(3,5-dichloro-4-hydroxyphenyl)-8-[[(2R)-2-(3,5-dichloro-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carbonyl]amino]-2-(4-hydroxyphenyl)acetate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 methyl (2R)-2-[[(8R,11R,14S)-8-[[(2R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetyl]amino]-11-(3,5-dichloro-4-hydroxyphenyl)-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carbonyl]amino]-2-(4-hydroxyphenyl)acetate
  参考文献：
  名称：

  补全他汀和氯肽I的非对映异构体的合成：分子内Suzuki-Miyaura反应的底物依赖性阻转异构体选择性。

  摘要：

  DOI：

  10.1002/anie.200800599