methyl (2S,4S,5R,6R)-5-acetamido-4-amino-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate;hydrochloride | 1360872-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-5-acetamido-4-amino-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate;hydrochloride
• CAS: 1360872-52-1
• 化学式: C₁₂H₂₂N₂O₈*ClH
• 分子量: 358.776
• InChiKey: ZKBHVFNJSKUKPZ-JYMIJESRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  172
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S,5R,6R)-5-acetamido-4-amino-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate;hydrochloride 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2R,3R,4S)-3-acetamido-4-[2-(1H-indol-3-yl)ethylcarbamothioylamino]-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
  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
• 作为产物：
  描述：

  methyl (4S,5R)-5-acetamido-4-((tert-butoxycarbonyl)amino)-2-oxo-5-((4S,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)pentanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-amino-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate;hydrochloride
  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

文献信息

• Concise synthesis of zanamivir and its C4-thiocarbamido derivatives utilizing a [3+2]-cycloadduct derived from d-glucono-δ-lactone
  作者：Xue-Bin Zhu、Meng Wang、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1016/j.tet.2012.01.011

  日期：2012.2

  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.