1-(4-hydroxyphenyl)-2-((3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethan-1-one | 1131344-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxyphenyl)-2-((3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethan-1-one
• CAS: 1131344-05-2
• 化学式: C₁₄H₁₈O₇
• 分子量: 298.293
• InChiKey: XUHRSNHJFFOOGT-ZLMOABSSSA-N

物化性质

• 沸点：
  604.4±55.0 °C(predicted)
• 密度：
  1.473±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127.45
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-2-((3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethan-1-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以75%的产率得到2-deoxy-2-(2-hydroxy-2-(4-hydroxyphenyl)ethyl)-D-glucose
  参考文献：
  名称：

  Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media

  摘要：

  The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane(TM)) was identified as the best activator of GAGs biosynthesis. Pro-Xylane(TM) was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.037
• 作为产物：
  描述：

  D-葡萄糖 、 1,3-bis-(4-hydroxyphenyl)-1,3-propanedione 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以34%的产率得到1-(4-hydroxyphenyl)-2-((3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethan-1-one
  参考文献：
  名称：

  Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media

  摘要：

  The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane(TM)) was identified as the best activator of GAGs biosynthesis. Pro-Xylane(TM) was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.037