(R)-3-amino-4,4-dimethoxybutanoic acid 1,1-dimethylethyl ester | 260051-90-9

• 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: (R)-3-amino-4,4-dimethoxybutanoic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl (3R)-3-amino-4,4-dimethoxybutanoate
• CAS: 260051-90-9
• 化学式: C₁₀H₂₁NO₄
• 分子量: 219.281
• InChiKey: PHLMCKPLJIGDIP-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (R)-3-amino-4,4-dimethoxybutanoic acid 1,1-dimethylethyl ester 在 吡啶 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以90%的产率得到(3R)-4,4-dimethoxy-3-{[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]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
• 作为产物：
  描述：

  (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester 在 palladium on activated charcoal (COCl₂)2 、 氢气 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， -45.0~20.0 ℃ 、101.33 kPa 条件下， 反应 49.0h， 生成 (R)-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