2,2'-(butane-1,4-diyl)bis<(2S,5R)-2,5'-dihydro-3,6-dimethoxy-5-isopropylpyrazine> | 218443-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 2,2'-(butane-1,4-diyl)bis<(2S,5R)-2,5'-dihydro-3,6-dimethoxy-5-isopropylpyrazine>
• 英文别名: (2S,5R)-2-[4-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]butyl]-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 218443-10-8
• 化学式: C₂₂H₃₈N₄O₄
• 分子量: 422.568
• InChiKey: AFTQYJQOOWMCOD-WNRNVDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2'-(butane-1,4-diyl)bis<(2S,5R)-2,5'-dihydro-3,6-dimethoxy-5-isopropylpyrazine> 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid dimethyl 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：

  1,4-二溴丁烷 、 (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 1,3-二甲基-2-咪唑啉酮 、 正丁基锂 作用下， 生成 (2S,5R)-2-[4-[(2R,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]butyl]-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine 、 2,2'-(butane-1,4-diyl)bis<(2S,5R)-2,5'-dihydro-3,6-dimethoxy-5-isopropylpyrazine>
  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).