1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]propan-2-one | 1131343-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]propan-2-one
• CAS: 1131343-97-9
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: JPPVLSHPYKNGBF-GLYPELGDSA-N

物化性质

• 沸点：
  369.9±42.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]propan-2-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以65%的产率得到1-(C-β-D-fucopyranosyl) propan-2-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
• 作为产物：
  描述：

  D-Fucose 、 乙酰丙酮 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 12.0h， 以92%的产率得到1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]propan-2-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

文献信息

• 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.