methyl 4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranoside | 399511-03-6

• 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: methyl 4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranoside
• 英文别名: (2S,3S,4aR,5R,6R,8R,8aR)-2,3,8-trimethoxy-2,3,6-trimethyl-5-phenylmethoxy-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxine
• CAS: 399511-03-6
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: NFIHIKLDVQVNMF-QTAXEDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  methyl 4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranoside 在 水 、 溶剂黄146 作用下， 反应 2.0h， 生成 methyl 4-O-benzyl-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：

  4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-L-fucopyranose 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到methyl 4-O-benzyl-2,3-O-(2,3-dimethoxybutane-2,3-diyl)-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

文献信息

• Synthesis of Carba- and C-Fucopyranosides and Their Evaluation as α-Fucosidase Inhibitors − Analysis of an Unusual Conformation Adopted by an Amino-C-fucopyranoside
  作者：Mercedes Carpintero、Agatha Bastida、Eduardo García-Junceda、Jesús Jiménez-Barbero、Alfonso Fernández-Mayoralas

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

  日期：2001.11

  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.