(2S,5R)-5-[(2R,4S)-5-Oxo-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-furan-2-ylmethyl]-pyrrolidine-2-carboxylic acid tert-butyl ester | 643014-03-3

• 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: (2S,5R)-5-[(2R,4S)-5-Oxo-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-furan-2-ylmethyl]-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS: 643014-03-3
• 化学式: C₁₆H₂₃F₃N₂O₅
• 分子量: 380.364
• InChiKey: SGXRJJIDVLCHRB-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-5-[(2R,4S)-5-Oxo-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-furan-2-ylmethyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 tert-butyl (3S,6S,8S,9aS)-8-hydroxy-6-(2,2,2-trifluoroacetylamino)-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
  参考文献：
  名称：

  Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins

  摘要：

  The (3S,6S,10S)-7/5 bicyclic lactam 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.170
• 作为产物：
  描述：

  (S)-N-benzyl-5-thioxoproline tert-butyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 生成 (2S,5R)-5-[(2R,4S)-5-Oxo-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-furan-2-ylmethyl]-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins

  摘要：

  The (3S,6S,10S)-7/5 bicyclic lactam 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.170