phenyl 2,3,4,6-tetra-O-methyl-β-D-selenogalactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-methyl-β-D-selenogalactopyranoside
• 英文别名: phenyl 2,3,4,6-tetra-O-methyl-1-seleno-β-D-galactopyranoside；(2R,3S,4S,5R,6S)-3,4,5-trimethoxy-2-(methoxymethyl)-6-phenylselanyloxane
• 化学式: C₁₆H₂₄O₅Se
• 分子量: 375.324
• InChiKey: DWXKDRJFNURQRT-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-胆甾烷醇 、 phenyl 2,3,4,6-tetra-O-methyl-β-D-selenogalactopyranoside 在 氧气 、 N-methylquinolinium hexafluorophosphate 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 cholestan-3β-yl 2,3,4,6-tetra-O-methyl-α-D-galactopyranoside 、 cholestan-3β-yl 2,3,4,6-tetra-O-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Photoinitiated Glycosylation at 350 nm

  摘要：

  A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1 -> 6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.

  DOI：

  10.1080/07328303.2011.601533
• 作为产物：
  描述：

  phenyl 1-seleno-β-D-galactopyranoside 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以4.26 g的产率得到phenyl 2,3,4,6-tetra-O-methyl-β-D-selenogalactopyranoside
  参考文献：
  名称：

  Photoinitiated Glycosylation at 350 nm

  摘要：

  A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1 -> 6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.

  DOI：

  10.1080/07328303.2011.601533

文献信息

• Korth, Hans-Gert; Sustmann, Reiner; Dupuis, Jacques, Journal of the Chemical Society. Perkin transactions II, 1986, p. 1453 - 1460
  作者：Korth, Hans-Gert、Sustmann, Reiner、Dupuis, Jacques、Giese, Bernd

  DOI：——

  日期：——
• Photoinitiated Glycosylation at 350 nm
  作者：Ian Cumpstey、David Crich

  DOI：10.1080/07328303.2011.601533

  日期：2011.9.1

  A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1 -> 6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.