(3S,6S,9aS)-6-[(2S)-2-(fluoren-9-ylmethoxycarbonylamino)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid | 643014-07-7

• 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: (3S,6S,9aS)-6-[(2S)-2-(fluoren-9-ylmethoxycarbonylamino)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid
• 英文别名: (3S,6S,9aS)-6-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylic acid
• CAS: 643014-07-7
• 化学式: C₃₀H₃₅N₃O₆
• 分子量: 533.624
• InChiKey: LGGLYSZMSNLSND-UZTPZCRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,6S,9aS)-6-[(2S)-2-(fluoren-9-ylmethoxycarbonylamino)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid 在 哌啶 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
  参考文献：
  名称：

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

  摘要：

  The (3S,6S, 10S)-7/5 bicyclic lactam 8, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. The cyclic peptide 35 containing the integrin recognition motif GLDV added across the amino and carboxyl groups of the lactam external constraint 8 was prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.037
• 作为产物：
  描述：

  methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate 在 palladium on activated charcoal 氯仿 、 叔丁基氯化镁 、 氢溴酸 、 氢气 、 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 128.0h， 生成 (3S,6S,9aS)-6-[(2S)-2-(fluoren-9-ylmethoxycarbonylamino)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid
  参考文献：
  名称：

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

  摘要：

  The (3S,6S, 10S)-7/5 bicyclic lactam 8, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. The cyclic peptide 35 containing the integrin recognition motif GLDV added across the amino and carboxyl groups of the lactam external constraint 8 was prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.037

文献信息

• Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins
  作者：David E. Davies、Paul M. Doyle、R.Duncan Farrant、Richard D. Hill、Peter B. Hitchcock、Paul N. Sanderson、Douglas W. Young

  DOI：10.1016/j.tetlet.2003.09.170

  日期：2003.12

  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.