(R)-2-((S)-1-Benzyloxycarbonylamino-ethyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester | 488833-73-4

• 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: (R)-2-((S)-1-Benzyloxycarbonylamino-ethyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
• 英文别名: methyl (4R)-2-[(1S)-1-(phenylmethoxycarbonylamino)ethyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 488833-73-4
• 化学式: C₁₅H₁₈N₂O₅
• 分子量: 306.318
• InChiKey: RTUWJJRJNPUJGO-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-((S)-1-Benzyloxycarbonylamino-ethyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 在 palladium on activated charcoal sodium cyanide 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (R)-2-{(S)-1-[(R)-2-({(S)-1-[(S)-3-(Diphenyl-phosphinothioyl)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-ethyl}-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Solid-phase synthesis of phosphine–oxazoline peptides

  摘要：

  An approach is presented that allows for the synthesis of phosphine-oxazoline ligands by solid-phase synthesis. The method involves the synthesis of amino oxazolines and their use in the cleavage of phosphine sulfide peptides from Kaiser oxime resin. It was discovered that the addition of a catalytic amount of sodium cyanide allows the nucleophilie cleavage from the resin to take place at room temperature and without the addition of acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01596-4
• 作为产物：
  描述：

  N-(N-phenylmethoxycarbonyl-L-alanyl)-D-serine methyl ester 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以93%的产率得到(R)-2-((S)-1-Benzyloxycarbonylamino-ethyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Solid-phase synthesis of phosphine–oxazoline peptides

  摘要：

  An approach is presented that allows for the synthesis of phosphine-oxazoline ligands by solid-phase synthesis. The method involves the synthesis of amino oxazolines and their use in the cleavage of phosphine sulfide peptides from Kaiser oxime resin. It was discovered that the addition of a catalytic amount of sodium cyanide allows the nucleophilie cleavage from the resin to take place at room temperature and without the addition of acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01596-4