(S,S)-2-<<(benzyloxy)carbonyl>amino>-7-<<(9H-fluoren-9-ylmethoxy)carbonyl>amino>octanedioic acid 1-(2-oxo-2-phenylethyl) ester | 218443-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S,S)-2-<<(benzyloxy)carbonyl>amino>-7-<<(9H-fluoren-9-ylmethoxy)carbonyl>amino>octanedioic acid 1-(2-oxo-2-phenylethyl) ester
• 英文别名: (2S,7S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-8-oxo-8-phenacyloxy-7-(phenylmethoxycarbonylamino)octanoic acid
• CAS: 218443-19-7
• 化学式: C₃₉H₃₈N₂O₉
• 分子量: 678.739
• InChiKey: USSHKJNUKPLURE-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S,S)-2-<<(benzyloxy)carbonyl>amino>-7-<<(9H-fluoren-9-ylmethoxy)carbonyl>amino>octanedioic acid 1-(2-oxo-2-phenylethyl) ester 在 氢溴酸 、 溶剂黄146 作用下， 反应 2.0h， 以99%的产率得到(S,S)-2-amino-7-<<(9H-fluoren-9-ylmethoxy)carbonyl>amino>octanedioic acid 1-(2-oxo-2-phenylethyl) ester
  参考文献：
  名称：

  Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine

  摘要：

  Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz = [(benzyloxy)carbonyl]), was obtained by means of Schollkopf bis-lactim ether methodology and optimized monoesterification procedures. Selective amino deprotection at the non-esterified amino-acid function of 7a by dichloromethyl-methyl-ether-induced 'N-carboxyanhydride' formation, and hydrolysis permitted access to the Boc/Cbz- and Fmoc/Cbz-protected monophenacyl esters 11a and 11b, as well as to the fully orthogonally protected Fmoc/Boc monophenacyl ester 12 (Boc = (teri-butoxy)carbonyl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl).

  DOI：

  10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 (S,S)-2-amino-7-<<(benzyloxy)carbonyl>amino>octanedioic acid 8-(2-oxo-2-phenylethyl) ester acetate salt 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以77%的产率得到(S,S)-2-<<(benzyloxy)carbonyl>amino>-7-<<(9H-fluoren-9-ylmethoxy)carbonyl>amino>octanedioic acid 1-(2-oxo-2-phenylethyl) ester
  参考文献：
  名称：

  Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine

  摘要：

  Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz = [(benzyloxy)carbonyl]), was obtained by means of Schollkopf bis-lactim ether methodology and optimized monoesterification procedures. Selective amino deprotection at the non-esterified amino-acid function of 7a by dichloromethyl-methyl-ether-induced 'N-carboxyanhydride' formation, and hydrolysis permitted access to the Boc/Cbz- and Fmoc/Cbz-protected monophenacyl esters 11a and 11b, as well as to the fully orthogonally protected Fmoc/Boc monophenacyl ester 12 (Boc = (teri-butoxy)carbonyl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl).

  DOI：

  10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4