1-(p-methoxybenzyloxy)-3-(prop-2-ynyloxy)-2,2-bis[(prop-2-ynyloxy)methyl]propane | 879015-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(p-methoxybenzyloxy)-3-(prop-2-ynyloxy)-2,2-bis[(prop-2-ynyloxy)methyl]propane
• 英文别名: 1-Methoxy-4-[[3-prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)propoxy]methyl]benzene
• CAS: 879015-72-2
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: NBRJGYPYYFXLAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(p-methoxybenzyloxy)-3-(prop-2-ynyloxy)-2,2-bis[(prop-2-ynyloxy)methyl]propane 、 1,9-bis(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)-5-(4-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy]-2-oxabutyl)-5-(p-iodophenoxymethyl)-3,7-dioxanonane 在 copper(l) iodide 、 四(三苯基膦)钯 二异丙胺 、 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以10 mg的产率得到(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-[2-[[4-[3-[2-[(4-methoxyphenyl)methoxymethyl]-3-[3-[4-[3-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]-2,2-bis[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxymethyl]propoxy]phenyl]prop-2-ynoxy]-2-[3-[4-[3-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]-2,2-bis[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxymethyl]propoxy]phenyl]prop-2-ynoxymethyl]propoxy]prop-1-ynyl]phenoxy]methyl]-3-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]-2-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxymethyl]propoxy]ethoxy]oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of a Nonavalent Mannoside Glycodendrimer Based on Pentaerythritol

  摘要：

  A nonavalent glycodendrimer bearing terminal alpha-D-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having three 2-hydroxyethyl ether substituents. Two efficient routes were developed for the synthesis of the pentaerythritol-based core (17), which has three terminal propargyl ethers. Conditions were found under which the triple Sonogashira coupling reaction of the dendron and the tri-O-propargyl ether (17) proceeded efficiently. The product was deprotected and it and precursors were fully characterized by NMR spectroscopy and FT-ICR mass spectrometry.

  DOI：

  10.1021/jo052045u
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-5,5-bis((prop-2-yn-1-yloxy)methyl)-1,3-dioxane 在 三乙基硅烷 、 二氯乙基铝 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.67h， 生成 1-(p-methoxybenzyloxy)-3-(prop-2-ynyloxy)-2,2-bis[(prop-2-ynyloxy)methyl]propane
  参考文献：
  名称：

  Synthesis of a Nonavalent Mannoside Glycodendrimer Based on Pentaerythritol

  摘要：

  A nonavalent glycodendrimer bearing terminal alpha-D-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having three 2-hydroxyethyl ether substituents. Two efficient routes were developed for the synthesis of the pentaerythritol-based core (17), which has three terminal propargyl ethers. Conditions were found under which the triple Sonogashira coupling reaction of the dendron and the tri-O-propargyl ether (17) proceeded efficiently. The product was deprotected and it and precursors were fully characterized by NMR spectroscopy and FT-ICR mass spectrometry.

  DOI：

  10.1021/jo052045u

文献信息

• Synthesis of a Nonavalent Mannoside Glycodendrimer Based on Pentaerythritol
  作者：Hussein Al-Mughaid、T. Bruce Grindley

  DOI：10.1021/jo052045u

  日期：2006.2.1

  A nonavalent glycodendrimer bearing terminal alpha-D-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having three 2-hydroxyethyl ether substituents. Two efficient routes were developed for the synthesis of the pentaerythritol-based core (17), which has three terminal propargyl ethers. Conditions were found under which the triple Sonogashira coupling reaction of the dendron and the tri-O-propargyl ether (17) proceeded efficiently. The product was deprotected and it and precursors were fully characterized by NMR spectroscopy and FT-ICR mass spectrometry.