N-((1R,2S,3R,4S,5R)-2-Fluoro-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide | 475639-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: N-((1R,2S,3R,4S,5R)-2-Fluoro-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide
• 英文别名: N-[(1R,2S,3R,4S,5R)-2-fluoro-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl]acetamide
• CAS: 475639-49-7
• 化学式: C₈H₁₂FNO₄
• 分子量: 205.186
• InChiKey: KDGUBKVPRSTGCE-QQGCVABSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-((1R,2S,3R,4S,5R)-2-Fluoro-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide 在 Lindlar catalyst 盐酸 、 sodium azide 、 N-acetylneuraminic acid aldolase 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 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 potassium hydrogen bifluoride 、 Bu₄NFH₂F₃ 、 Dowex 50W (H+) 作用下， 以28%的产率得到N-((1R,2S,3R,4S,5R)-2-Fluoro-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide
  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

文献信息

• Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives
  作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Yoshiyuki Kobayashi、Makoto Yamashita

  DOI：10.1016/s0960-894x(02)00328-1

  日期：2002.8

  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.