diethyl (2S,3R)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate | 101924-55-4

• 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: diethyl (2S,3R)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate
• 英文别名: diethyl(2R,3S)-2-hydroxy-3-(N-t-Boc-amino)butanedioate；diethyl erythro-3-hydroxy-N-(tertbutoxycarbonyl)-L-aspartate；diethyl (2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 101924-55-4
• 化学式: C₁₃H₂₃NO₇
• 分子量: 305.328
• InChiKey: VZTHIICJZUVGAH-DTWKUNHWSA-N

物化性质

• 沸点：
  432.5±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  diethyl (2S,3R)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以82%的产率得到(2S,3R)-3-hydroxyaspartic acid hydrochloride
  参考文献：
  名称：

  Activity of the enantiomers of erythro-3-hydroxyaspartate at glutamate transporters and NMDA receptors

  摘要：

  AbstractThe enantiomers of erythro‐3‐hydroxyaspartate were tested for activity at glutamate transporters and NMDA receptors. Both enantiomers inhibited glutamate transporters in rat hippocampal crude synaptosomes and elicited substrate‐like activity at excitatory amino acid transporter 1, 2, and 3 as measured by voltage clamp in the Xenopus oocyte expression system. The enantiomers had similar affinities, but the D‐enantiomer showed a lower maximal effect at excitatory amino acid transporter 1, 2, and 3 than the L‐enantiomer. Surprisingly, D‐erythro‐3‐hydroxyaspartate was a potent NMDA receptor agonist with an EC50 value in rat hippocampal neurons of 320 nM, whereas the L‐enantiomer was 100‐fold less potent. L‐erythro‐3‐hydroxyaspartate showed activity at both glutamate transporters and NMDA receptors at concentrations that are reported to inhibit serine racemase, indicating a lack of selectivity. This enantiomeric pair may assist in shedding further light on the structural requirements for substrate activity at glutamate transporters and for agonist activity at NMDA receptors. imageThe erythro enantiomers of 3‐hydroxyaspartate had interesting and surprising effects on glutamate neurotransmitter systems. L‐erythro‐3‐hydroxyaspartate had activity at both glutamate transporters (EAAT1/2/3) and NMDA receptors. D‐erythro‐3‐hydroxyaspartate acted on EAATs, but was also identified as a highly potent NMDA receptor agonist. These enantiomers shed further light on the structural requirements for activity at EAATs and NMDA receptors.

  DOI：

  10.1111/jnc.13430
• 作为产物：
  描述：

  L-(+)-酒石酸二乙酯 在 氯化亚砜 、 palladium 10% on activated carbon 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 diethyl (2S,3R)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate
  参考文献：
  名称：

  有效制备β-羟基天冬氨酸及其衍生物

  摘要：

  摘要我们报道了一种有效且实用的合成路线，可以合成各种得到适当保护的赤藓-β-OH-Asp化合物，这些化合物是珊瑚霉素A和其他肽类天然产物中的关键β支链α-氨基酸单元。由廉价的手性前体酒石酸1-二乙酯酒石酸酯经六步制备Fmoc和环状缩酮保护的赤藓糖-β-OH-Asp7，而无需进行柱纯化。7的修饰形式可作为erythreo-β-OH-Asp的各种β-烷氧基类似物的通用前体。此外，我们成功地完成了对珊瑚霉素A的全合成的模型研究，其特征是在后期安装了erythreo-β-OMe-Asn的侧链伯酰胺基。

  DOI：

  10.1016/j.cclet.2018.05.012

文献信息

• DIETHYL (2S,3R)-2-(N-tert-BUTOXYCARBONYL)AMINO- 3-HYDROXYSUCCINATE
  作者：Saito, Seiki、Komada, Kanji、Moriwake, Toshio、Fox, Martin、Overman, Larry E.

  DOI：10.15227/orgsyn.073.0184

  日期：——
• A facile cleavage of oxirane with hydrazoic acid in dmf A new route to chiral β-hydroxy-α-amino acids
  作者：Seiki Saito、Norio Bunya、Masami Inaba、Toshio Moriwake、Sigeru Torii

  DOI：10.1016/s0040-4039(00)95024-x

  日期：——
• Efficient preparation of β-hydroxy aspartic acid and its derivatives
  作者：Long Liu、Bo Wang、Cheng Bi、Gang He、Gong Chen

  DOI：10.1016/j.cclet.2018.05.012

  日期：2018.7

  Abstract We report an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched α-amino acid units in coralmycin A and other peptide natural products. Fmoc and cyclic ketal-protected erythreo-β-OH-Asp 7 is prepared from cheap chiral precursor l -diethyl tartrate in six steps without the need of column purification. The modified form

  摘要我们报道了一种有效且实用的合成路线，可以合成各种得到适当保护的赤藓-β-OH-Asp化合物，这些化合物是珊瑚霉素A和其他肽类天然产物中的关键β支链α-氨基酸单元。由廉价的手性前体酒石酸1-二乙酯酒石酸酯经六步制备Fmoc和环状缩酮保护的赤藓糖-β-OH-Asp7，而无需进行柱纯化。7的修饰形式可作为erythreo-β-OH-Asp的各种β-烷氧基类似物的通用前体。此外，我们成功地完成了对珊瑚霉素A的全合成的模型研究，其特征是在后期安装了erythreo-β-OMe-Asn的侧链伯酰胺基。
• Activity of the enantiomers of erythro-3-hydroxyaspartate at glutamate transporters and NMDA receptors
  作者：Alan C. Foster、Yong-Xin Li、Stephen Runyan、Tim Dinh、Steven Venadas、June Chen、Srinath Pashikanti、Apurba Datta、George Ehring、Ursula Staubli

  DOI：10.1111/jnc.13430

  日期：2016.2

  AbstractThe enantiomers of erythro‐3‐hydroxyaspartate were tested for activity at glutamate transporters and NMDA receptors. Both enantiomers inhibited glutamate transporters in rat hippocampal crude synaptosomes and elicited substrate‐like activity at excitatory amino acid transporter 1, 2, and 3 as measured by voltage clamp in the Xenopus oocyte expression system. The enantiomers had similar affinities, but the D‐enantiomer showed a lower maximal effect at excitatory amino acid transporter 1, 2, and 3 than the L‐enantiomer. Surprisingly, D‐erythro‐3‐hydroxyaspartate was a potent NMDA receptor agonist with an EC50 value in rat hippocampal neurons of 320 nM, whereas the L‐enantiomer was 100‐fold less potent. L‐erythro‐3‐hydroxyaspartate showed activity at both glutamate transporters and NMDA receptors at concentrations that are reported to inhibit serine racemase, indicating a lack of selectivity. This enantiomeric pair may assist in shedding further light on the structural requirements for substrate activity at glutamate transporters and for agonist activity at NMDA receptors. imageThe erythro enantiomers of 3‐hydroxyaspartate had interesting and surprising effects on glutamate neurotransmitter systems. L‐erythro‐3‐hydroxyaspartate had activity at both glutamate transporters (EAAT1/2/3) and NMDA receptors. D‐erythro‐3‐hydroxyaspartate acted on EAATs, but was also identified as a highly potent NMDA receptor agonist. These enantiomers shed further light on the structural requirements for activity at EAATs and NMDA receptors.