allyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside | 147157-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-3,4,5-tris[(4-methoxyphenyl)methoxy]-2-methyl-6-prop-2-enoxyoxane
• CAS: 147157-86-6
• 化学式: C₃₃H₄₀O₈
• 分子量: 564.676
• InChiKey: OAWFTFNITLYATP-UAWMXBIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside 在 Wilkinson's catalyst 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 (Z)-propenyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside 、 (E)-propenyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors

  摘要：

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.

  DOI：

  10.1002/prac.19923340706
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 ion exchange resin IR-120 (H⁺ form) 、 sodium hydride 作用下， 反应 20.0h， 生成 allyl-2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors

  摘要：

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.

  DOI：

  10.1002/prac.19923340706

文献信息

• Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors
  作者：Horst Kunz、Carlo Unverzagt

  DOI：10.1002/prac.19923340706

  日期：——

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.