(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 548759-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 548759-72-4
• 化学式: C₂₇H₄₅NO₁₂
• 分子量: 575.654
• InChiKey: QRSBJLCULLPNDW-XPTJXIRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  146.31
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 四氧化锇 、 Grubbs catalyst first generation 、 sodium azide 、 Dowex 50W (H⁺) 、 硫酸 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三甲氧基磷 作用下， 以 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 生成 (2R,3R,4R,2'S,3'R,4'R)-3',4'-Diacetoxy-3-acetylamino-4-azido-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：

  2-(2,2-diethyl[1,3]dioxolan-4-yl)ethanol 在 吡啶 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-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