5-[(p-bromophenoxy)methyl]-5-[(2-hydroxyethoxy)methyl]-3,7-dioxa-1,9-nonanediol | 879015-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[(p-bromophenoxy)methyl]-5-[(2-hydroxyethoxy)methyl]-3,7-dioxa-1,9-nonanediol
• 英文别名: 2-[2-[(4-Bromophenoxy)methyl]-3-(2-hydroxyethoxy)-2-(2-hydroxyethoxymethyl)propoxy]ethanol
• CAS: 879015-67-5
• 化学式: C₁₇H₂₇BrO₇
• 分子量: 423.301
• InChiKey: RKFCDHSYOYGSEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[(p-bromophenoxy)methyl]-5-[(2-hydroxyethoxy)methyl]-3,7-dioxa-1,9-nonanediol 、 [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以86%的产率得到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-bromophenoxymethyl)-3,7-dioxanonane
  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：

  季戊四醇三烯丙基醚 在 吡啶 、 sodium hydroxide 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 5-[(p-bromophenoxy)methyl]-5-[(2-hydroxyethoxy)methyl]-3,7-dioxa-1,9-nonanediol
  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.