3-(C-glucosyl)-2-propanone | 1095832-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(C-glucosyl)-2-propanone
• 英文别名: 1-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]propan-2-one
• CAS: 1095832-56-6
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: XMNOVTHWCLGVID-HFYYSOHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(C-glucosyl)-2-propanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以88%的产率得到1-(C-β-D-glucopyranosyl)-2-hydroxypropane
  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 、 乙酰丙酮 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 12.0h， 以100%的产率得到3-(C-glucosyl)-2-propanone
  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

文献信息

• C-GLYCOSIDE COMPOUNDS, AND METHOD FOR PREPARING C-GLYCOSIDE COMPOUNDS
  申请人：Benvegnu Thierry

  公开号：US20110245490A1

  公开（公告）日：2011-10-06

  The invention relates to C-glycose compounds of formula (I) where: S′ is a monosaccharide radical or a polysaccharide radical derived from a monosaccharide or polysaccharide S; R is a linear or branched alkyl radical; and Z is an ethylenyl CH═CR1(R2) or an acetylenyl C≡CR3 radical. The invention also relates to a method for preparing C-glycoside compounds of formula (III), characterised in that the method consists of a step of reacting a sugar (S), in an aqueous solvent or in the absence of a solvent and in the presence of an organic or mineral base (B), with a phosphonate of formula (II) according to the following reaction pattern: Formulas (II), (III).

  该发明涉及公式（I）的C-葡聚糖化合物，其中：S′是单糖基或从单糖或多糖S衍生的多糖基；R是直链或支链烷基基团；Z是乙烯基CH═CR1（R2）或乙炔基C≡CR3基团。该发明还涉及一种制备公式（III）的C-葡聚糖化合物的方法，其特征在于该方法包括以下反应模式：公式（II），（III）。
• Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media
  作者：Alexandre Cavezza、Christophe Boulle、Amélie Guéguiniat、Patrick Pichaud、Simon Trouille、Louis Ricard、Maria Dalko-Csiba

  DOI：10.1016/j.bmcl.2008.12.037

  日期：2009.2

  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.