methyl (2S,3S,4S,5R,6R)-3,5-dibenzoyloxy-6-[(2R,3S,4R,5R,6R)-3-benzoyloxy-2-(benzoyloxymethyl)-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4-methoxyoxane-2-carboxylate | 1198406-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,3S,4S,5R,6R)-3,5-dibenzoyloxy-6-[(2R,3S,4R,5R,6R)-3-benzoyloxy-2-(benzoyloxymethyl)-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4-methoxyoxane-2-carboxylate
• CAS: 1198406-10-8
• 化学式: C₅₆H₅₀Cl₃NO₁₇
• 分子量: 1115.37
• InChiKey: WQFAHQMALGAURV-VBBNDMPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  77
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  216
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-3,5-dibenzoyloxy-6-[(2R,3S,4R,5R,6R)-3-benzoyloxy-2-(benzoyloxymethyl)-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4-methoxyoxane-2-carboxylate 、 乙酸酐 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%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：

  [(2R,3S,4R,5R,6R)-3-benzoyloxy-4-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate 、 methyl (2S,3S,4S,5R,6R)-3,5-dibenzoyloxy-4-methoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以83%的产率得到methyl (2S,3S,4S,5R,6R)-3,5-dibenzoyloxy-6-[(2R,3S,4R,5R,6R)-3-benzoyloxy-2-(benzoyloxymethyl)-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4-methoxyoxane-2-carboxylate
  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