N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester | 103300-55-6

• 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: N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester
• CAS: 103300-55-6；124510-62-9；124510-63-0；124510-64-1；124510-65-2
• 化学式: C₃₇H₄₂N₂O₇
• 分子量: 626.75
• InChiKey: UGZVYSSKFOGOBG-ULVBUKFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以74%的产率得到(3S)-3-amino-4-oxo-4-[[2-oxo-1-phenyl-2-[[(1R,2S)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]oxy]ethyl]amino]butanoic acid
  参考文献：
  名称：

  High potency dipeptide sweeteners. 1. L-Aspartyl-D-phenylglycine esters

  摘要：

  Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxy-phenylglycine ester, were prepared. The L-aspartyl-D-phenylglycine (-)-alpha- and (+)-beta-fenchyl esters had the highest sweetness potency at 1200 and 3700 times that of sucrose, respectively. The high potency of these sweeteners is surprising as the phenyl group occupies a position previously believed to accommodate only much smaller groups.

  DOI：

  10.1021/jm00165a027
• 作为产物：
  描述：

  N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine (-)-α-fenchyl ester 在 盐酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.0h， 生成 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester
  参考文献：
  名称：

  High potency dipeptide sweeteners. 1. L-Aspartyl-D-phenylglycine esters

  摘要：

  Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxy-phenylglycine ester, were prepared. The L-aspartyl-D-phenylglycine (-)-alpha- and (+)-beta-fenchyl esters had the highest sweetness potency at 1200 and 3700 times that of sucrose, respectively. The high potency of these sweeteners is surprising as the phenyl group occupies a position previously believed to accommodate only much smaller groups.

  DOI：

  10.1021/jm00165a027