diethyl (2R, 3S)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate | 101924-63-4

• 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 (2R, 3S)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate
• 英文别名: diethyl (2S,3R)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 101924-63-4
• 化学式: C₁₃H₂₃NO₇
• 分子量: 305.328
• InChiKey: VZTHIICJZUVGAH-BDAKNGLRSA-N

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 (2R, 3S)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以76%的产率得到(2R,3S)-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：

  1-[(1R,2S)-3-ethoxy-1-(ethoxycarbonyl)-2-hydroxy-3-oxopropyl]-1,2-triazadien-2-ium 在 palladium on activated charcoal 氢气 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 diethyl (2R, 3S)-2-(N-tert-butoxycarbonyl)amino-3-hydroxysuccinate
  参考文献：
  名称：

  A facile cleavage of oxirane with hydrazoic acid in dmf A new route to chiral β-hydroxy-α-amino acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)95024-x

文献信息

• Process for the production of pentostatin aglycone and pentostatin
  申请人：——

  公开号：US20040181052A1

  公开（公告）日：2004-09-16

  A novel, scaleable and improved process for preparing pentostatin and its analogs is disclosed. The method comprises the diastereospecific synthesis of the nucleobase from commercially available L-Dialkyl tartarates.

  揭示了一种用于制备戊糖核苷和其类似物的新型、可扩展和改进的工艺。该方法包括从市售的L-二烷基酒石酸盐合成核碱的对映体特异性合成。
• US7393954B2
  申请人：——

  公开号：US7393954B2

  公开（公告）日：2008-07-01