[(2R,3S,4R,5R,6R)-3-benzoyloxy-4-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate | 1194331-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6R)-3-benzoyloxy-4-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate
• CAS: 1194331-57-1
• 化学式: C₃₄H₃₀Cl₃NO₉
• 分子量: 702.972
• InChiKey: JMKXMXONWPZQFS-VPNCTUESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  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 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以89%的产率得到
  参考文献：
  名称：

  The first chemical synthesis of F-4-GlcAβ(1→3)GlcNAc-UDP with the potential of novel substrate and enzyme inhibitor for hyaluronic acid synthases (HASs)

  摘要：

  The first chemical synthesis of F-4-GlcA beta(1 -> 3)GlcNAc-UDP is described here. This compound can serve as a novel substrate to study the catalytic mechanism of hyaluronic acid synthases (HASs) and has potential to be donor for these enzymes that extend HA chain at the reducing end. Moreover, it may also behave as inhibitor for the enzymes that act on non-reducing end in the assembly of HA chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.017
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到[(2R,3S,4R,5R,6R)-3-benzoyloxy-4-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate
  参考文献：
  名称：

  The first chemical synthesis of F-4-GlcAβ(1→3)GlcNAc-UDP with the potential of novel substrate and enzyme inhibitor for hyaluronic acid synthases (HASs)

  摘要：

  The first chemical synthesis of F-4-GlcA beta(1 -> 3)GlcNAc-UDP is described here. This compound can serve as a novel substrate to study the catalytic mechanism of hyaluronic acid synthases (HASs) and has potential to be donor for these enzymes that extend HA chain at the reducing end. Moreover, it may also behave as inhibitor for the enzymes that act on non-reducing end in the assembly of HA chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.017

文献信息

• The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)
  作者：Guohua Wei、Vipin Kumar、Jun Xue、Robert D. Locke、Khushi L. Matta

  DOI：10.1016/j.tetlet.2009.09.042

  日期：2009.11

  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