N-((2R,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide | 1226768-12-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: N-((2R,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide
• 英文别名: (S)-N-[(2R,3S)-4-hydroxy-1-nitro-3-pentan-3-yloxybutan-2-yl]-2-methylpropane-2-sulfinamide
• CAS: 1226768-12-2
• 化学式: C₁₃H₂₈N₂O₅S
• 分子量: 324.442
• InChiKey: VCSMSSWWUMXKLP-ZSMADZGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((2R,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide 在 盐酸 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 C₉H₂₀N₂O₄
  参考文献：
  名称：

  A Practical and Azide-Free Synthetic Approach to Oseltamivir from Diethyl d-Tartrate

  摘要：

  A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.

  DOI：

  10.1021/jo100187m
• 作为产物：
  描述：

  硝基甲烷 、 N-((S,S(S))-3-hydroxy-2-(pentan-3-yloxy)propylidene)-2-methylpropane-2-sulfinamide 在 sodium hydroxide 作用下， 反应 24.0h， 生成 N-((2S,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide 、 N-((2R,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  A Practical and Azide-Free Synthetic Approach to Oseltamivir from Diethyl d-Tartrate

  摘要：

  A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.

  DOI：

  10.1021/jo100187m

文献信息

• Process for the preparation of 1-nitro-4-oxobutanylamides
  申请人：Synkola, s.r.o.

  公开号：EP2385034B1

  公开（公告）日：2015-12-02
• A Practical and Azide-Free Synthetic Approach to Oseltamivir from Diethyl <scp>d</scp>-Tartrate
  作者：Jiang Weng、Yong-Bo Li、Rui-Bin Wang、Feng-Quan Li、Can Liu、Albert S. C. Chan、Gui Lu

  DOI：10.1021/jo100187m

  日期：2010.5.7

  A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.