(S)-1-((S)-2-tert-Butoxycarbonylamino-4-hydroxy-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester | 363599-61-5

• 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: (S)-1-((S)-2-tert-Butoxycarbonylamino-4-hydroxy-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
• 英文别名: Boc-Hse-Pyr-OEt；ethyl (2S)-1-[(2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 363599-61-5
• 化学式: C₁₆H₂₆N₂O₇
• 分子量: 358.392
• InChiKey: FMAQDTXMDIPRLR-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-1-((S)-2-tert-Butoxycarbonylamino-4-hydroxy-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-1-((S)-2-tert-Butoxycarbonylamino-4-hydroxy-butyryl)-5-hydroxy-pyrrolidine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  A convenient and versatile synthesis of 6,5- and 7,5-fused bicyclic lactams as peptidomimetics

  摘要：

  Chemo-selective reduction of the pyroglutamate ring carbonyl in a serine-pyroglutamate or homoserine to pyroglutamate dipeptide gave a hemiaminal. Treatment of the hemiaminal with a catalytic amount of TFA in CH,CI, generated an N-acyliminium ion that was intramolecularly trapped by the side-chain hydroxyl to give a 6.5 or 7,5-bicyclic lactam. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00909-1
• 作为产物：
  描述：

  N-叔丁氧羰基-O-苄基-L-高丝氨酸 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-1-((S)-2-tert-Butoxycarbonylamino-4-hydroxy-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  A convenient and versatile synthesis of 6,5- and 7,5-fused bicyclic lactams as peptidomimetics

  摘要：

  Chemo-selective reduction of the pyroglutamate ring carbonyl in a serine-pyroglutamate or homoserine to pyroglutamate dipeptide gave a hemiaminal. Treatment of the hemiaminal with a catalytic amount of TFA in CH,CI, generated an N-acyliminium ion that was intramolecularly trapped by the side-chain hydroxyl to give a 6.5 or 7,5-bicyclic lactam. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00909-1