methyl (2S,3S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[2-[(1R,2S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-1,3-thiazole-4-carbonyl]amino]pentanoyl]amino]butanoate | 1432520-36-9

• 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,3S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[2-[(1R,2S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-1,3-thiazole-4-carbonyl]amino]pentanoyl]amino]butanoate
• CAS: 1432520-36-9
• 化学式: C₂₅H₄₂N₄O₇S
• 分子量: 542.697
• InChiKey: BZNJJPZUSVKPCE-NLQHDTCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  184
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[2-[(1R,2S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-1,3-thiazole-4-carbonyl]amino]pentanoyl]amino]butanoate 在 盐酸 、 4-二甲氨基吡啶 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 2-(((2S,3S)-2-((2S,3S)-2-(2-((1R,2S)-1-amino-2-methylbutyl)thiazole-4-carboxamido)-3-methylpentanamido)-3-hydroxybutanamido)methyl)thiazole-4-carboxylic acid
  参考文献：
  名称：

  First total synthesis of aerucyclamide B

  摘要：

  The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-L-allo-Thr-L-Ile-Thz-D-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the beta-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%). (C)13 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.060
• 作为产物：
  描述：

  Boc-L-Ile-L-aThr-OMe 在 盐酸 、 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 methyl (2S,3S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[2-[(1R,2S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-1,3-thiazole-4-carbonyl]amino]pentanoyl]amino]butanoate
  参考文献：
  名称：

  First total synthesis of aerucyclamide B

  摘要：

  The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-L-allo-Thr-L-Ile-Thz-D-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the beta-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%). (C)13 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.060

文献信息

• First total synthesis of aerucyclamide B
  作者：Stella Peña、Laura Scarone、Eduardo Manta、Gloria Serra

  DOI：10.1016/j.tetlet.2013.03.060

  日期：2013.5

  The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-L-allo-Thr-L-Ile-Thz-D-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the beta-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%). (C)13 Elsevier Ltd. All rights reserved.