benzyl ((S)-1-((R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl) carbonate | 1150100-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl ((S)-1-((R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl) carbonate
• CAS: 1150100-21-2
• 化学式: C₂₈H₂₆O₈
• 分子量: 490.51
• InChiKey: PLVPBOQRTKLEQH-BJKOFHAPSA-N

物化性质

• 沸点：
  744.8±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 benzyl ((S)-1-((R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl) carbonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以321 g的产率得到4-((S)-2-(((benzyloxy)carbonyl)oxy)-2-((R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)ethoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects

  摘要：

  Collagen is critical for skin strength and elasticity, and its degradation leads to wrinkles that accompany aging. Based emphasis on the aesthetics, we tried to make a new compound that can highly stimulate collagen biosynthesis and synthesized ascorbyl conjugated peptide that is a complex form connected by succinoyl linker. We conducted several in vitro and in vivo experiments to identify if the compound has a potent activity, comparing to the ascorbic acid only for collagen biosynthesis. Our in vitro and in vivo result identified that ascorbyl conjugated peptide can stimulate collagen biosynthesis in human dermis and is assumably stable in the rat skin extracts. In conclusion, we strongly suggest that ascorbyl conjugated peptide can be used as a main ingredient for cosmetic products as well as wound healing agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.112
• 作为产物：
  描述：

  benzyl ((S)-1-((R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-(trityloxy)ethyl) carbonate 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 生成 benzyl ((S)-1-((R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl) carbonate
  参考文献：
  名称：

  Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects

  摘要：

  Collagen is critical for skin strength and elasticity, and its degradation leads to wrinkles that accompany aging. Based emphasis on the aesthetics, we tried to make a new compound that can highly stimulate collagen biosynthesis and synthesized ascorbyl conjugated peptide that is a complex form connected by succinoyl linker. We conducted several in vitro and in vivo experiments to identify if the compound has a potent activity, comparing to the ascorbic acid only for collagen biosynthesis. Our in vitro and in vivo result identified that ascorbyl conjugated peptide can stimulate collagen biosynthesis in human dermis and is assumably stable in the rat skin extracts. In conclusion, we strongly suggest that ascorbyl conjugated peptide can be used as a main ingredient for cosmetic products as well as wound healing agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.112