3-Acetamino-3-desoxy-1,2-O-isopropyliden-α-D-ribofuranose | 29881-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Acetamino-3-desoxy-1,2-O-isopropyliden-α-D-ribofuranose
• 英文别名: 3-Acetamino-3-deoxy-1,2-O-isopropyliden-α-D-ribofuranose；N-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetamide
• CAS: 29881-53-6
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: NGDMCQAAEDAQDO-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Acetamino-3-desoxy-1,2-O-isopropyliden-α-D-ribofuranose 、 苯甲醇 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲苯 、 水 为溶剂， 反应 24.0h， 生成 O-benzyl-3-acetamido-3-deoxy-β-D-ribofuranoside 、 O-benzyl-3-acetamido-3-deoxy-α-D-ribofuranoside
  参考文献：
  名称：

  [EN] SYNTHESIS OF OSELTAMIVIR CONTAINING PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY
  [FR] SYNTHÈSE D'OSELTAMIVIR CONTENANT DES CONGÉNÈRES DE PHOSPHONATE AYANT UNE ACTIVITÉ ANTI-GRIPPALE

  摘要：

  公开号：

  WO2009029888A3
• 作为产物：
  描述：

  3-amino-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以2.35 g的产率得到3-Acetamino-3-desoxy-1,2-O-isopropyliden-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of Tamiflu and its Phosphonate Congeners Possessing Potent Anti-Influenza Activity

  摘要：

  Using D-xylose as an appropriate chiral precursor, we have synthesized active neuraminidase inhibitor oseltamivir, antiflu drug Tamiflu, and novel phosphonate congeners that exhibit even stronger antiflu activities by inhibiting the neuraminidases of the wildtype and H274Y mutant of H1N1 and H5N1 viruses. Molecular modeling of the neuraminidase-phosphonate complex indicates a pertinent binding mode of the phosphonate with three arginine residues in the active site. Discovery of such potent neuraminidase inhibitors will offer an opportunity to the development of new anti-influenza drugs.

  DOI：

  10.1021/ja073992i

文献信息

• [EN] SYNTHESIS OF OSELTAMIVIR CONTAINING PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY<br/>[FR] SYNTHÈSE D'OSELTAMIVIR CONTENANT DES CONGÉNÈRES DE PHOSPHONATE AYANT UNE ACTIVITÉ ANTI-GRIPPALE
  申请人：WONG CHI-HUEY

  公开号：WO2009029888A3

  公开（公告）日：2009-05-07
• Synthesis of Tamiflu and its Phosphonate Congeners Possessing Potent Anti-Influenza Activity
  作者：Jiun-Jie Shie、Jim-Min Fang、Shi-Yun Wang、Keng-Chang Tsai、Yih-Shyun E. Cheng、An-Suei Yang、Shih-Chia Hsiao、Ching-Yao Su、Chi-Huey Wong

  DOI：10.1021/ja073992i

  日期：2007.10.1

  Using D-xylose as an appropriate chiral precursor, we have synthesized active neuraminidase inhibitor oseltamivir, antiflu drug Tamiflu, and novel phosphonate congeners that exhibit even stronger antiflu activities by inhibiting the neuraminidases of the wildtype and H274Y mutant of H1N1 and H5N1 viruses. Molecular modeling of the neuraminidase-phosphonate complex indicates a pertinent binding mode of the phosphonate with three arginine residues in the active site. Discovery of such potent neuraminidase inhibitors will offer an opportunity to the development of new anti-influenza drugs.