(2R,3R,4S,2'R,4'S,5'R)-4',5'-Diacetoxy-3-acetylamino-4-(2,2-dimethyl-propionyloxy)-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester | 548759-82-6

• 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: (2R,3R,4S,2'R,4'S,5'R)-4',5'-Diacetoxy-3-acetylamino-4-(2,2-dimethyl-propionyloxy)-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester
• CAS: 548759-82-6
• 化学式: C₂₃H₃₃NO₁₁
• 分子量: 499.515
• InChiKey: ZYUQIJMRHRMSMD-VBQNUUEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,2'R,4'S,5'R)-4',5'-Diacetoxy-3-acetylamino-4-(2,2-dimethyl-propionyloxy)-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester 在 Lindlar's catalyst sodium azide 、 Dowex 50W (H⁺) 、 氢气 作用下， 以 乙醇 、 叔丁醇 为溶剂， 生成 (2R,3R,4R,2'R,4'S,5'R)-4',5'-Diacetoxy-3-acetylamino-4-amino-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9
• 作为产物：
  描述：

  乙酸酐 、 (2R,3R,4S,6S,2'R,4'S,5'R)-3-Acetylamino-4-(2,2-dimethyl-propionyloxy)-4',5'-dihydroxy-6-methoxy-octahydro-[2,2']bipyranyl-6-carboxylic acid methyl ester 在 硫酸 、 溶剂黄146 作用下， 生成 (2R,3R,4S,2'R,4'S,5'R)-4',5'-Diacetoxy-3-acetylamino-4-(2,2-dimethyl-propionyloxy)-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9