(2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-(methyloxycarbonylmethyl)butanoic acid methyl ester | 349148-41-0

• 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: (2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-(methyloxycarbonylmethyl)butanoic acid methyl ester
• 英文别名: dimethyl (2R)-2-[(1S)-2-hydroxy-1-(phenylmethoxycarbonylamino)ethyl]butanedioate
• CAS: 349148-41-0
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: FXDVWPYIPQSZQH-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-(methyloxycarbonylmethyl)butanoic acid methyl ester 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到(2R,3S)-3,4-(benzyloxycarbonylimino)-2-(methyloxycarbonylmethyl)butanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle

  摘要：

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

  DOI：

  10.1021/jo0014055
• 作为产物：
  描述：

  (2S,3R)-2-Benzyloxycarbonylamino-3-methoxycarbonyl-pentanedioic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 5-methyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-(methyloxycarbonylmethyl)butanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle

  摘要：

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

  DOI：

  10.1021/jo0014055