2,6-difluoro-N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)[2-hydroxy-4-(phenylmethoxy)phenyl]methanimine N-oxide | 191280-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-difluoro-N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)[2-hydroxy-4-(phenylmethoxy)phenyl]methanimine N-oxide
• CAS: 191280-99-6
• 化学式: C₂₆H₂₉F₂NO₈
• 分子量: 521.515
• InChiKey: OCIBKMYIEGYADK-SSYDHYAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethylsulfoxonium methylide 、 2,6-difluoro-N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)[2-hydroxy-4-(phenylmethoxy)phenyl]methanimine N-oxide 以 四氢呋喃 为溶剂， 生成 6-(2,6-Difluoro-benzyloxy)-3-(2-methanesulfinyl-ethyl)-2,3-dihydro-benzofuran 、 N-[(S)-6-(2,6-Difluoro-benzyloxy)-2,3-dihydro-benzofuran-3-yl]-N-[(3aS,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-hydroxylamine 、 N-[(R)-6-(2,6-Difluoro-benzyloxy)-2,3-dihydro-benzofuran-3-yl]-N-[(3aS,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-hydroxylamine
  参考文献：
  名称：

  Enantioselective Synthesis of 5-LO Inhibitor Hydroxyureas. Tandem Nucleophilic Addition−Intramolecular Cyclization of Chiral Nitrones

  摘要：

  An enantioselective synthesis of chiral hydroxyurea based 5-lipoxygenase inhibitors is reported via a five-step sequence in about 39% overall yield. The synthesis is based on a novel tandem nucleophilic addition-intramolecular cyclization reaction in which a chiral nitrone functions as the electrophilic acceptor species. A mannose-based chiral auxiliary controls the diastereoselectivity of the reaction in an 8:1 ratio. After the auxiliary removal and appropriate functionalization, a single recrystallization afforded the target structures in > 99% ee.

  DOI：

  10.1021/jo9621736
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 三正丁胺 、 碳酸氢钠 、 potassium iodide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 2,6-difluoro-N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)[2-hydroxy-4-(phenylmethoxy)phenyl]methanimine N-oxide
  参考文献：
  名称：

  Enantioselective Synthesis of 5-LO Inhibitor Hydroxyureas. Tandem Nucleophilic Addition−Intramolecular Cyclization of Chiral Nitrones

  摘要：

  An enantioselective synthesis of chiral hydroxyurea based 5-lipoxygenase inhibitors is reported via a five-step sequence in about 39% overall yield. The synthesis is based on a novel tandem nucleophilic addition-intramolecular cyclization reaction in which a chiral nitrone functions as the electrophilic acceptor species. A mannose-based chiral auxiliary controls the diastereoselectivity of the reaction in an 8:1 ratio. After the auxiliary removal and appropriate functionalization, a single recrystallization afforded the target structures in > 99% ee.

  DOI：

  10.1021/jo9621736