(S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid 2-oxo-2-phenylethyl ester | 1028300-26-6

• 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: (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid 2-oxo-2-phenylethyl ester
• 英文别名: (2S,7S)-8-oxo-8-phenacyloxy-2,7-bis(phenylmethoxycarbonylamino)octanoic acid
• CAS: 1028300-26-6
• 化学式: C₃₂H₃₄N₂O₉
• 分子量: 590.63
• InChiKey: UJDBDJTWTHERTC-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid 2-oxo-2-phenylethyl ester 在 1,1-二氯甲醚 作用下， 反应 2.5h， 以100%的产率得到(S,S)-7-amino-2-<<(benzyloxy)carbonyl>amino>octanedioic acid 1-(2-oxo-2-phenylethyl) ester 7-(N-carboxyanhydride)
  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：

  (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid 、 2-溴苯乙酮 以 1,4-二氧六环 、 水 为溶剂， 反应 96.0h， 生成 (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid 2-oxo-2-phenylethyl ester 、 (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid bis(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

文献信息

• Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine
  作者：Meinolf Lange、Peter M. Fischer

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

  日期：1998.11.11

  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).