N-[(2R,3R,4R,5S,6R)-2-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide | 737766-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4R,5S,6R)-2-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
• CAS: 737766-08-4
• 化学式: C₁₄H₂₅NO₈
• 分子量: 335.354
• InChiKey: YNEZTWICQYGLBC-XBKPPWAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  126.71
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R,4R,5S,6R)-2-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide 在 三甲基铵三氧化硫共聚物 、 三氟乙酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase

  摘要：

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.013
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-[(2R,3R,4R,5S,6R)-2-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase

  摘要：

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.013