(2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1198406-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1198406-07-3
• 化学式: C₂₄H₂₆O₁₀
• 分子量: 474.464
• InChiKey: HOQDLWAWNGSKBA-VZGLXOSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 反应 6.0h， 以90%的产率得到
  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-萘甲醇 、 3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  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