methyl (2S)-3-methyl-2-[[(2R,3S)-3-methyl-2-[[2-[2-[2-[2-[2-[(1S)-2-[(2-methylpropan-2-yl)oxy]-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-1,3-thiazol-4-yl]-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carbonyl]amino]pentanoyl]amino]butanoate | 952413-90-0

• 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: methyl (2S)-3-methyl-2-[[(2R,3S)-3-methyl-2-[[2-[2-[2-[2-[2-[(1S)-2-[(2-methylpropan-2-yl)oxy]-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-1,3-thiazol-4-yl]-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carbonyl]amino]pentanoyl]amino]butanoate
• CAS: 952413-90-0
• 化学式: C₄₅H₅₄N₈O₁₁S
• 分子量: 915.037
• InChiKey: FANDMFXWYOXNMF-URZSDBKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  65
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  277
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-methyl-2-[[(2R,3S)-3-methyl-2-[[2-[2-[2-[2-[2-[(1S)-2-[(2-methylpropan-2-yl)oxy]-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-1,3-thiazol-4-yl]-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carbonyl]amino]pentanoyl]amino]butanoate 在 lithium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 (20R,23S,26S)-20-[(2S)-butan-2-yl]-26-[(2-methylpropan-2-yl)oxymethyl]-16-phenyl-23-propan-2-yl-3,11,15,28-tetraoxa-7-thia-19,22,25,30,31,32,33,34-octazahexacyclo[25.2.1.12,5.16,9.110,13.114,17]tetratriaconta-1(29),2(34),4,6(33),8,10(32),12,14(31),16,27(30)-decaene-18,21,24-trione
  参考文献：
  名称：

  Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization

  摘要：

  Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.103
• 作为产物：
  描述：

  methyl 2'-(2-bromo-1,1-dimethoxyethyl)-5-phenyl-[2,4']bis-oxazolyl-4-carboxylate 在 lithium hydroxide 、 甲酸 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 methyl (2S)-3-methyl-2-[[(2R,3S)-3-methyl-2-[[2-[2-[2-[2-[2-[(1S)-2-[(2-methylpropan-2-yl)oxy]-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-1,3-thiazol-4-yl]-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carbonyl]amino]pentanoyl]amino]butanoate
  参考文献：
  名称：

  Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization

  摘要：

  Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.103

文献信息

• Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization
  作者：Delia Hernández、Estela Riego、Andrés Francesch、Carmen Cuevas、Fernando Albericio、Mercedes Álvarez

  DOI：10.1016/j.tet.2007.06.103

  日期：2007.9

  Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. (C) 2007 Elsevier Ltd. All rights reserved.