(R)-2-((S)-2-Isobutyrylamino-3-mercapto-2-methyl-propionylamino)-3-mercapto-N-[(R)-2-mercapto-1-(2-mercapto-ethylcarbamoyl)-1-methyl-ethyl]-2-methyl-propionamide | 177546-80-4

• 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: (R)-2-((S)-2-Isobutyrylamino-3-mercapto-2-methyl-propionylamino)-3-mercapto-N-[(R)-2-mercapto-1-(2-mercapto-ethylcarbamoyl)-1-methyl-ethyl]-2-methyl-propionamide
• 英文别名: (2R)-2-methyl-2-[[(2R)-2-methyl-2-[[(2S)-2-methyl-2-(2-methylpropanoylamino)-3-sulfanylpropanoyl]amino]-3-sulfanylpropanoyl]amino]-3-sulfanyl-N-(2-sulfanylethyl)propanamide
• CAS: 177546-80-4
• 化学式: C₁₈H₃₄N₄O₄S₄
• 分子量: 498.756
• InChiKey: ULYSNOKRISWARI-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  120
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-((S)-2-Isobutyrylamino-3-mercapto-2-methyl-propionylamino)-3-mercapto-N-[(R)-2-mercapto-1-(2-mercapto-ethylcarbamoyl)-1-methyl-ethyl]-2-methyl-propionamide 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以10 mg的产率得到(4R,4'S,4''R)-2''-Isopropyl-4,4',4''-trimethyl-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazole-4-carboxylic acid (2-mercapto-ethyl)-amide
  参考文献：
  名称：

  Convergent Synthesis of (−)-Mirabazole C Using a Chloroimidazolidium Coupling Reagent, CIP

  摘要：

  Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three a-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of alpha,alpha-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an alpha,alpha-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.

  DOI：

  10.1021/jo952285h
• 作为产物：
  描述：

  N-(2-methylpropionyl)-S-benzyl-(S)-2-methylcysteinyl-S-benzyl-(R)-methylcysteinyl-S-benzyl-(R)-methylcysteine N-((benzylthio)ethyl)amide 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-2-((S)-2-Isobutyrylamino-3-mercapto-2-methyl-propionylamino)-3-mercapto-N-[(R)-2-mercapto-1-(2-mercapto-ethylcarbamoyl)-1-methyl-ethyl]-2-methyl-propionamide
  参考文献：
  名称：

  Convergent Synthesis of (−)-Mirabazole C Using a Chloroimidazolidium Coupling Reagent, CIP

  摘要：

  Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three a-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of alpha,alpha-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an alpha,alpha-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.

  DOI：

  10.1021/jo952285h

文献信息

• Convergent Synthesis of (−)-Mirabazole C Using a Chloroimidazolidium Coupling Reagent, CIP
  作者：Kenichi Akaji、Naohiro Kuriyama、Yoshiaki Kiso

  DOI：10.1021/jo952285h

  日期：1996.1.1

  Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three a-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of alpha,alpha-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an alpha,alpha-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.