(1S,3R,4R,5S,8S)-4,8-dihydroxy-3-(naphthalen-2-ylmethoxy)-2,6-dioxabicyclo[3.2.1]octan-7-one | 1198406-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,3R,4R,5S,8S)-4,8-dihydroxy-3-(naphthalen-2-ylmethoxy)-2,6-dioxabicyclo[3.2.1]octan-7-one
• CAS: 1198406-16-4
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: QSEBIKCPXGYAKM-CEEVZKBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5S,8S)-4,8-dihydroxy-3-(naphthalen-2-ylmethoxy)-2,6-dioxabicyclo[3.2.1]octan-7-one 、 苯甲酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以96%的产率得到(1S,3R,4R,5S,8S)-3-(naphthalen-2-ylmethoxy)-7-oxo-2,6-dioxabicyclo[3.2.1]octane-4,8-diyl dibenzoate
  参考文献：
  名称：

  The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

  摘要：

  The first chemical synthesis of MeO-3-GluUA beta(1 -> 3)GlcNAc-UDP to elucidate the catalytic mechanism of hyalyionic acid synthases (HASS) is described. Construction of the desired beta(1 -> 3)-linked disaccharide 10 was achieved very efficiently by Coupling MeO-3-GlcUA donor 3 with the suitable protected GlCnt(10C) acceptor 4 using BF3 Et2O as Lewis acid Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetlet.2009.09.042
• 作为产物：
  描述：

  2'-naphthalenemethyl β-D-glucopyranosiduronic acid 在 苯甲酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以86%的产率得到(1S,3R,4R,5S,8S)-4,8-dihydroxy-3-(naphthalen-2-ylmethoxy)-2,6-dioxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

  摘要：

  The first chemical synthesis of MeO-3-GluUA beta(1 -> 3)GlcNAc-UDP to elucidate the catalytic mechanism of hyalyionic acid synthases (HASS) is described. Construction of the desired beta(1 -> 3)-linked disaccharide 10 was achieved very efficiently by Coupling MeO-3-GlcUA donor 3 with the suitable protected GlCnt(10C) acceptor 4 using BF3 Et2O as Lewis acid Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetlet.2009.09.042