H-Abu-Sar-N(Me)Leu-Val-N(Me)Leu-Ala-OBn.HCl | 1356203-91-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-Abu-Sar-N(Me)Leu-Val-N(Me)Leu-Ala-OBn.HCl
• 英文别名: benzyl (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-aminobutanoyl]-methylamino]acetyl]-methylamino]-4-methylpentanoyl]amino]-3-methylbutanoyl]-methylamino]-4-methylpentanoyl]amino]propanoate;hydrochloride
• CAS: 1356203-91-2
• 化学式: C₃₆H₆₀N₆O₇*ClH
• 分子量: 725.369
• InChiKey: FNOWCYRLRCDCGB-AEVONIPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  171
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  H-Abu-Sar-N(Me)Leu-Val-N(Me)Leu-Ala-OBn.HCl 、 Boc-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octensaeure 在 异氰酸叔丁酯 作用下， 以 氯仿 为溶剂， 反应 0.75h， 以45 mg的产率得到(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester
  参考文献：
  名称：

  Expanding the Limits of Isonitrile-Mediated Amidations: On the Remarkable Stereosubtleties of Macrolactam Formation from Synthetic Seco-Cyclosporins

  摘要：

  The scope of isonitrile-mediated amide bond-forming reactions is further explored in this second-generation synthetic approach to cyclosporine (cyclosporin A). Both type I and type II amidations are utilized in this effort, allowing access to epimeric cyclosporins A and H from a single precursor by variation of the coupling reagents. This work lends deeper insight into the relative acylating ability of the formimidate carboxylate mixed anhydride (FCMA) intermediate, while shedding light on the far-reaching impact of remote stereochemical changes on the effective preorganization of seco-cyclosporins.

  DOI：

  10.1021/ja2103372
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester 在 盐酸 、 异氰环已烷 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 1.26h， 生成 H-Abu-Sar-N(Me)Leu-Val-N(Me)Leu-Ala-OBn.HCl
  参考文献：
  名称：

  Expanding the Limits of Isonitrile-Mediated Amidations: On the Remarkable Stereosubtleties of Macrolactam Formation from Synthetic Seco-Cyclosporins

  摘要：

  The scope of isonitrile-mediated amide bond-forming reactions is further explored in this second-generation synthetic approach to cyclosporine (cyclosporin A). Both type I and type II amidations are utilized in this effort, allowing access to epimeric cyclosporins A and H from a single precursor by variation of the coupling reagents. This work lends deeper insight into the relative acylating ability of the formimidate carboxylate mixed anhydride (FCMA) intermediate, while shedding light on the far-reaching impact of remote stereochemical changes on the effective preorganization of seco-cyclosporins.

  DOI：

  10.1021/ja2103372