(2S,3S)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester | 149598-19-6

• 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: (2S,3S)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester
• 英文别名: dimethyl (2S,3S)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 149598-19-6
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: UYRDCVHVAHEWBD-YUMQZZPRSA-N

物化性质

• 沸点：
  365.4±32.0 °C(predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 以94%的产率得到(+/-)-threo-3-methylaspartic acid
  参考文献：
  名称：

  Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane

  摘要：

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.157
• 作为产物：
  描述：

  重氮甲烷 、 (2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-succinic acid 1-methyl ester 以 乙醚 为溶剂， 反应 0.25h， 以100%的产率得到(2S,3S)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane

  摘要：

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.157

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.
• Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane
  作者：Kazuhiko Sakaguchi、Masahiro Yamamoto、Tetsuo Kawamoto、Takeshi Yamada、Tetsuro Shinada、Keiko Shimamoto、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2004.05.157

  日期：2004.7

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.