(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-[[(2S)-2-[[(2S)-2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoic acid | 336854-68-3

• 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: (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-[[(2S)-2-[[(2S)-2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoic acid
• CAS: 336854-68-3
• 化学式: C₆₀H₈₄N₁₀O₂₀
• 分子量: 1265.38
• InChiKey: CWDVOJIDPJBMOA-KLRKOEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  90
• 可旋转键数：
  36
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  436
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-[[(2S)-2-[[(2S)-2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoic acid 在 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 2-Chloro-1,3-dimethylimidazolidinium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent

  摘要：

  The synthesis of MEN11420, a potent tachykinin receptor antagonist, has been achieved. The bicyclic glycosylated structure of MEN11420 was constructed via intramolecular double cyclization using CIP-mediated activation. The head to tail cyclization of the linear precursor, which contained an cy-amino acid at its C-terminus, proceeded so rapidly that no serious racemization was apparent at the activated carboxyl function. The desired product was obtained without the need for purification of the intermediates throughout the synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00011-4
• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 、 Fmoc-L-天冬氨酸 beta-叔丁酯 、 Fmoc-L-色氨酸 、 N-(9-芴甲氧羰基)-N’-(2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-beta-D-吡喃葡萄糖基)-L-天冬酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 以95 mg的产率得到(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-[[(2S)-2-[[(2S)-2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent

  摘要：

  The synthesis of MEN11420, a potent tachykinin receptor antagonist, has been achieved. The bicyclic glycosylated structure of MEN11420 was constructed via intramolecular double cyclization using CIP-mediated activation. The head to tail cyclization of the linear precursor, which contained an cy-amino acid at its C-terminus, proceeded so rapidly that no serious racemization was apparent at the activated carboxyl function. The desired product was obtained without the need for purification of the intermediates throughout the synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00011-4