N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester | 116050-32-9

• 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 (-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester
• 英文别名: N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-endo-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl ester；benzyl (3S)-4-oxo-4-[[(1R)-2-oxo-1-phenyl-2-[[(1R,2R,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]oxy]ethyl]amino]-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 116050-32-9
• 化学式: C₃₆H₄₀N₂O₈
• 分子量: 628.722
• InChiKey: DDCKFGMEUXFWPX-WMRGRJQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 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：
  0.39
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以66%的产率得到L-aspartyl-D-phenylglycine (-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl 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
• 作为产物：
  描述：

  (+/-)-exo-2-hydroxy-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptane 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 24.5h， 生成 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl 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

文献信息

• JANUSZ, J. M.;GARDLIK, J. M.;YOUNG, P. A.;BURKES, R. V.;STOLL, S. J.;ESTE+, J. MED. CHEM., 33,(1990) N, C. 1052-1061
  作者：JANUSZ, J. M.、GARDLIK, J. M.、YOUNG, P. A.、BURKES, R. V.、STOLL, S. J.、ESTE+

  DOI：——

  日期：——