(2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-methylbutanoic acid methyl ester | 349148-40-9

• 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-methylbutanoic acid methyl ester
• 英文别名: methyl (2R,3S)-4-hydroxy-2-methyl-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 349148-40-9
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: AZEFTZILFPJMLA-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-methylbutanoic acid methyl ester 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(3R,4S)-3-methyl-4-N-(benzyloxycarbonylamino)butyrolactone
  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：

  BOC-L-天冬氨酸二甲酯 在 sodium tetrahydroborate 、 sodium carbonate 、 乙酰氯 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 36.0h， 生成 (2R,3S)-3-(benzyloxycarbonylamino)-4-hydroxy-2-methylbutanoic 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

文献信息

• Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle
  作者：Jeong-il Park、Guan Rong Tian、Dong H. Kim

  DOI：10.1021/jo0014055

  日期：2001.6.1

  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.