methyl (1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate | 1402746-27-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-hydroxy-2-pentan-3-yloxy-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1402746-27-3
• 化学式: C₁₄H₂₃NO₆
• 分子量: 301.34
• InChiKey: DFCFIWIORGOFCV-ZKYQVNSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 1-(pent-3-yl) 2-acetamido-3-O-acetyl-2,4-dideoxy-α-L-threo-hex-4-enopyranosiduronic acid
  参考文献：
  名称：

  Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

  摘要：

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

  DOI：

  10.1021/jm301145k
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium bromide 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 160.25h， 生成 methyl (1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate
  参考文献：
  名称：

  Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

  摘要：

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

  DOI：

  10.1021/jm301145k

文献信息

• Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase
  作者：Beenu Bhatt、Raphael Böhm、Philip S. Kerry、Jeffrey C. Dyason、Rupert J. M. Russell、Robin J. Thomson、Mark von Itzstein

  DOI：10.1021/jm301145k

  日期：2012.10.25

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.