HCl*D-Nle-OBzl | 173204-47-2

• 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: HCl*D-Nle-OBzl
• 英文别名: D-norleucine benzyl ester; hydrochloride；D-Norleucin-benzylester; Hydrochlorid
• CAS: 173204-47-2
• 化学式: C₁₃H₁₉NO₂*ClH
• 分子量: 257.76
• InChiKey: XXGPFHINPVSQFP-UTONKHPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  HCl*D-Nle-OBzl 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-cis-2,6-dimethylpiperidinocarbonyl-γ-methylleucyl-D-1-(methoxycarbonyl)tryptophanyl-D-norleucine
  参考文献：
  名称：

  An Efficient Preparation of the Pseudopeptide Endothelin-B Receptor Selective Antagonist BQ-788

  摘要：

  The endothelins are a family of bicyclic 21 amino acid peptides that are potent and prolonged vasoconstrictors. BQ-788 is a modified tripeptide that is the only known highly potent and selective antagonist for the endothelin-B (ET(B)) receptor subtype discovered to date. Previous preparations of BQ-788 (N-(cis-2,6-dimethylpiperidinocarbonyl)-gamma-methylleucyl-D-1-(methoxycarbonyl)tryptophanyl-D-norleucine sodium salt) have suffered from several synthetic difficulties, including formation of the sterically hindered N-(cis-2,6-dimethylpiperidinocarbonyl)-gamma-methylleucine, racemization of tryptophan during carbamination, and the facile reduction of the indole ring of tryptophan during catalytic hydrogenation. In order to prepare sufficient quantities of BQ-788 for in vitro and in vivo evaluations of the physiological significance of the ET(B) receptor, we have developed an efficient solution phase multiple-gram synthetic strategy.

  DOI：

  10.1021/jo00130a028
• 作为产物：
  描述：

  benzyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 HCl*D-Nle-OBzl
  参考文献：
  名称：

  An Efficient Preparation of the Pseudopeptide Endothelin-B Receptor Selective Antagonist BQ-788

  摘要：

  The endothelins are a family of bicyclic 21 amino acid peptides that are potent and prolonged vasoconstrictors. BQ-788 is a modified tripeptide that is the only known highly potent and selective antagonist for the endothelin-B (ET(B)) receptor subtype discovered to date. Previous preparations of BQ-788 (N-(cis-2,6-dimethylpiperidinocarbonyl)-gamma-methylleucyl-D-1-(methoxycarbonyl)tryptophanyl-D-norleucine sodium salt) have suffered from several synthetic difficulties, including formation of the sterically hindered N-(cis-2,6-dimethylpiperidinocarbonyl)-gamma-methylleucine, racemization of tryptophan during carbamination, and the facile reduction of the indole ring of tryptophan during catalytic hydrogenation. In order to prepare sufficient quantities of BQ-788 for in vitro and in vivo evaluations of the physiological significance of the ET(B) receptor, we have developed an efficient solution phase multiple-gram synthetic strategy.

  DOI：

  10.1021/jo00130a028