(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-hydroxypropyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol | 952052-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-hydroxypropyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 952052-61-8
• 化学式: C₁₅H₂₈O₁₁
• 分子量: 384.381
• InChiKey: XDRQXGXBIJMYHB-CJWNZBJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-(C-lactosyl)-2-propanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以65%的产率得到(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-hydroxypropyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  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.