(2R,3R,4S)-3-acetamido-4-(3-(thiophen-2-ylmethyl)thioureido)-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid | 1360872-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,3R,4S)-3-acetamido-4-(3-(thiophen-2-ylmethyl)thioureido)-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1360872-55-4
• 化学式: C₁₇H₂₃N₃O₇S₂
• 分子量: 445.518
• InChiKey: HHGWBTUJIHTZFS-PWRGDLIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  160.38
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  methyl (2R,3R,4S)-3-acetamido-4-(thiophen-2-ylmethylcarbamothioylamino)-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以77%的产率得到(2R,3R,4S)-3-acetamido-4-(3-(thiophen-2-ylmethyl)thioureido)-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid
  参考文献：
  名称：

  Concise synthesis of zanamivir and its C4-thiocarbamido derivatives utilizing a [3+2]-cycloadduct derived from d-glucono-δ-lactone

  摘要：

  A concise synthesis of zanamivir (GG167, 1) has been accomplished utilizing the adduct of a highly diastereoselective 1,3-dipolar cycloaddition between methyl acrylate and the nitrone derived from D-glucono-delta-lactone. Azide-free introduction of C4 nitrogen functionality and one-pot selective O-acetylation followed by straightforward generation of dihydropyran moiety are two advantages in this synthesis. Using the established methodology and common intermediate, two representative C4-thiocarbamido derivatives of zanamivir were also synthesized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.011