(4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-2,3-diacetoxy-1-fluoro-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 174771-93-8

• 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: (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-2,3-diacetoxy-1-fluoro-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-[(1S,2R)-2,3-diacetyloxy-1-fluoropropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 174771-93-8
• 化学式: C₁₈H₂₄FNO₁₀
• 分子量: 433.388
• InChiKey: JDWDMZBDNWXPJJ-HCVDEJBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-2,3-diacetoxy-1-fluoro-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 Lindlar catalyst sodium azide 、 Dowex 50W (H+) 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 5-acetamido-4-(N,N'-bis-t-butoxycarbonylguanidino)-8,9-di-O-acetyl-2,3,4,5,7-pentadeoxy-7-fluoro-D-glycero-D-galacto-non-2-enopyranosoate
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1
• 作为产物：
  描述：

  2-acetamido-1,6:3,4-dianhydro-2-deoxy-β-D-talopyranose 在 盐酸 、 N-acetylneuraminic acid aldolase 、 potassium hydrogen bifluoride 、 Bu₄NFH₂F₃ 、 Dowex 50W (H+) 、 硫酸 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 生成 (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-2,3-diacetoxy-1-fluoro-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1