allyl 3-O-(4-methoxybenzyl)-2,4-di-O-methyl-α-L-fucopyranoside | 136737-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-(4-methoxybenzyl)-2,4-di-O-methyl-α-L-fucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-3,5-dimethoxy-4-[(4-methoxyphenyl)methoxy]-2-methyl-6-prop-2-enoxyoxane
• CAS: 136737-64-9
• 化学式: C₁₉H₂₈O₆
• 分子量: 352.428
• InChiKey: MLCNRNZTZHDEFA-QHWILLEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 3-O-(4-methoxybenzyl)-2,4-di-O-methyl-α-L-fucopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.5h， 以98%的产率得到allyl 2,4-di-O-methyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens

  摘要：

  Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.

  DOI：

  10.1016/0008-6215(92)84172-o
• 作为产物：
  描述：

  allyl 2-O-methyl-α-L-fucopyranoside 在 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 反应 5.5h， 生成 allyl 3-O-(4-methoxybenzyl)-2,4-di-O-methyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens

  摘要：

  Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.

  DOI：

  10.1016/0008-6215(92)84172-o