(2S,3S,4S,5R,6R)-4-hydroxy-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate | 1198406-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3S,4S,5R,6R)-4-hydroxy-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate
• CAS: 1198406-08-4
• 化学式: C₃₂H₂₈O₉
• 分子量: 556.569
• InChiKey: NUFXZJWRUAGLSM-AWKPRQMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-4-hydroxy-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate 、 碘甲烷 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以92%的产率得到(2S,3S,4S,5R,6R)-4-methoxy-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,5-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：

  甲醇 、 (1S,3R,4R,5S,8S)-3-(naphthalen-2-ylmethoxy)-7-oxo-2,6-dioxabicyclo[3.2.1]octane-4,8-diyl dibenzoate 在 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以92%的产率得到(2S,3S,4S,5R,6R)-4-hydroxy-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,5-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