(2R,3R)-3-(pentan-3-yloxy) butane-1,2,4-triol | 1226768-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-3-(pentan-3-yloxy) butane-1,2,4-triol
• 英文别名: (2R,3R)-3-pentan-3-yloxybutane-1,2,4-triol
• CAS: 1226768-09-7
• 化学式: C₉H₂₀O₄
• 分子量: 192.255
• InChiKey: AIZULODNMPFDCZ-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(pentan-3-yloxy) butane-1,2,4-triol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 以95%的产率得到(R)-3-hydroxy-2-(pentan-3-yloxy)propanal
  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：

  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

文献信息

• 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.