(2S,3R,4S,5R,6R)-2-cyclohexyloxy-6-(hydroxymethyl)oxane-3,4,5-triol | 477254-10-7

• 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-cyclohexyloxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 477254-10-7
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: PUEQSGBQJWWOQJ-IIRVCBMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  but-2-ynyl β-D-galactopyranoside 、 环己醇 在 gold(III) chloride 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 (2S,3R,4S,5R,6R)-2-cyclohexyloxy-6-(hydroxymethyl)oxane-3,4,5-triol 、 cyclohexyl-β-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation Using Unprotected Alkynyl Donors

  摘要：

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.

  DOI：

  10.1021/jo901857x

文献信息

• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.