(RS)-4,4-dimethoxy-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester | 183439-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-4,4-dimethoxy-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl 4,4-dimethoxy-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 183439-49-8
• 化学式: C₁₈H₂₇NO₆
• 分子量: 353.415
• InChiKey: KGBHPQZFCMHKMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (RS)-4,4-dimethoxy-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 48.0h， 生成 (RS)-3-amino-4,4-dimethoxybutanoic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Enantiomeric Purity of Protectedα-Amino and Peptide Aldehydes

  摘要：

  The synthesis of enantiomerically pure Ac-Tyr-Val-Ala-Asp(O'Bu)-H dimethyl acetal ((S)-1) is reported, a protected tetrapeptide C-terminal aldehyde belonging to a class of potent, reversible inhibitors of cysteine proteases (e.g.. interleukin-1 beta-converting enzyme (ICE), also called caspase-1). The coupling of the precursors Ac-Tyr-Val-Ala-OH ((S)-8) and H-Asp(O'Bu)-H dimethyl acetal ((S)-6) gave (S)-1 in a yield of 85%, with epimerization of < 2% at the alanine and aspartic-acid residue. (S)-6 itself was synthesized in four steps in an overall yield of 83% with an ee >98%.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1960::aid-hlca1960>3.0.co;2-2
• 作为产物：
  描述：

  Cbz-aspartic acid (tert-butyl ester) 在 N-甲基吗啉 、 sodium tetrahydroborate 、 (COCl₂)2 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.33h， 生成 (RS)-4,4-dimethoxy-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Enantiomeric Purity of Protectedα-Amino and Peptide Aldehydes

  摘要：

  The synthesis of enantiomerically pure Ac-Tyr-Val-Ala-Asp(O'Bu)-H dimethyl acetal ((S)-1) is reported, a protected tetrapeptide C-terminal aldehyde belonging to a class of potent, reversible inhibitors of cysteine proteases (e.g.. interleukin-1 beta-converting enzyme (ICE), also called caspase-1). The coupling of the precursors Ac-Tyr-Val-Ala-OH ((S)-8) and H-Asp(O'Bu)-H dimethyl acetal ((S)-6) gave (S)-1 in a yield of 85%, with epimerization of < 2% at the alanine and aspartic-acid residue. (S)-6 itself was synthesized in four steps in an overall yield of 83% with an ee >98%.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1960::aid-hlca1960>3.0.co;2-2