(S)-1-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester | 363599-59-1

• 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)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
• 英文别名: Boc-Hse(Bn)-Pyr-OEt；ethyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxybutanoyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 363599-59-1
• 化学式: C₂₃H₃₂N₂O₇
• 分子量: 448.516
• InChiKey: AFZKRPHESHHYGA-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-1-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 、 三氟乙酸 氢气 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4S,7S,9aS)-4-tert-Butoxycarbonylamino-5-oxo-octahydro-pyrrolo[2,1-b][1,3]oxazepine-7-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 、 sodium salt of (S)-ethyl pyroglutamate 生成 (S)-1-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-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

文献信息

• A convenient and versatile synthesis of 6,5- and 7,5-fused bicyclic lactams as peptidomimetics
  作者：Xiaojun Zhang、Wen Jiang、Aaron C. Schmitt

  DOI：10.1016/s0040-4039(01)00909-1

  日期：2001.7

  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.