diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate | 1226768-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate
• 英文别名: 4,5-Diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate
• CAS: 1226768-08-6
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: FWASNAKBEXBREB-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 potassium hydroxide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 以88%的产率得到(2R,3R)-3-(pentan-3-yloxy) butane-1,2,4-triol
  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：

  3,3-dimethoxypentane 、 D-(-)-酒石酸二乙酯 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以96%的产率得到diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate
  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.