4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranose | 399510-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranose
• 英文别名: (2S,3S,4aR,5R,6R,8R,8aR)-2,3-dimethoxy-2,3,6-trimethyl-5-phenylmethoxy-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-8-ol
• CAS: 399510-98-6
• 化学式: C₂₀H₃₀O₆
• 分子量: 366.455
• InChiKey: DTSIIOLLFVAWNW-ZSGYZSAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranose 在 palladium on activated charcoal 水 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 L-glycero-2,3-dihydroxypropyl 5a-carba-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of Carba- and C-Fucopyranosides and Their Evaluation as α-Fucosidase Inhibitors − Analysis of an Unusual Conformation Adopted by an Amino-C-fucopyranoside

  摘要：

  Several carba- and C-fucopyranosides bearing a variety of substituents at their pseudoanomeric positions have been synthesized and tested as inhibitors of bovine kidney a-fucosidase. From the IC50 values, some conclusions about the structure-activity relationship could be drawn, The presence of a hydroxyl group close to the pseudoanomeric position, or the presence of an aromatic ring as substituent, were beneficial for inhibitory activity. A 1-(R)-amino-phenylmethyl C-fucopyranoside, the activity of which increased 40 times when the pH was changed from 5.0 to 7.0, adopted a C-4(1) conformation, in contrast to the C-1(4) form normally adopted by natural fucopyranosides. The conformation of this compound was analyzed in comparison with that of the 1-(S)-configured epimer, using NMR spectroscopy and molecular modeling.

  DOI：

  10.1002/1099-0690(200111)2001:21<4127::aid-ejoc4127>3.0.co;2-6
• 作为产物：
  描述：

  2,3-丁二酮 、 4-O-benzyl-5a-carba-α-L-fucopyranose 、 原甲酸三甲酯 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranose
  参考文献：
  名称：

  Synthesis of Carba- and C-Fucopyranosides and Their Evaluation as α-Fucosidase Inhibitors − Analysis of an Unusual Conformation Adopted by an Amino-C-fucopyranoside

  摘要：

  Several carba- and C-fucopyranosides bearing a variety of substituents at their pseudoanomeric positions have been synthesized and tested as inhibitors of bovine kidney a-fucosidase. From the IC50 values, some conclusions about the structure-activity relationship could be drawn, The presence of a hydroxyl group close to the pseudoanomeric position, or the presence of an aromatic ring as substituent, were beneficial for inhibitory activity. A 1-(R)-amino-phenylmethyl C-fucopyranoside, the activity of which increased 40 times when the pH was changed from 5.0 to 7.0, adopted a C-4(1) conformation, in contrast to the C-1(4) form normally adopted by natural fucopyranosides. The conformation of this compound was analyzed in comparison with that of the 1-(S)-configured epimer, using NMR spectroscopy and molecular modeling.

  DOI：

  10.1002/1099-0690(200111)2001:21<4127::aid-ejoc4127>3.0.co;2-6