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 | 1360872-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 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
• CAS: 1360872-56-5
• 化学式: C₂₉H₃₆N₄O₁₀S
• 分子量: 632.692
• InChiKey: ZKIBZHVTINRHHA-QZAJBKBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  216
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  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 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以69%的产率得到(2R,3R,4S)-3-acetamido-4-[2-(1H-indol-3-yl)ethylcarbamothioylamino]-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
• 作为产物：
  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