1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranose | 214117-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranose
• 英文别名: [(1R,2R,3R,4R,5R)-4-azido-2-(trifluoromethylsulfonyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl] benzoate
• CAS: 214117-33-6
• 化学式: C₁₄H₁₂F₃N₃O₇S
• 分子量: 423.326
• InChiKey: YLVFCFXUFYWYTF-BZNQNGANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranose 在 硫脲 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of S-Linked Thiooligosaccharide Analogues of Nodulation Factors. 2.¹ Synthesis of an Intermediate Thiotrisaccharide

  摘要：

  An S-linked thiotrisaccharide analogue of chitin that carries different N-protecting groups at the reducing and nonreducing end glucosamine residues was prepared as an intermediate for the synthesis of thioanalogues of nodulation factors. 1,6-Anhydro-2-azido-3-O-benzoyl-2-deoxy-beta-D-glucopyranose (3) was prepared either through the nucleophilic displacement of the 4-triflate galacto analogue 1 with potassium chloroacetate or via the selective acylation of the analogous gluco diol 4. Condensation of 3 with the N-phthalimido trichloroacetimidate 9 led to the disaccharide 10, which was converted in four steps to the glucosyl bromide 15. Nucleophilic displacement of the anomeric bromide by a 4-thiolate derivative of glucosamine (16) bearing a trichloroethoxycarbamate at C-2 was performed in anhydrous oxygen-free THF and led to the desired thiotrisaccharide precursor of thioanalogues of nodulation factors. Alternatively, the disaccharide 10 was prepared by regioselective glycosylation of the 1,6-anhydro diol 4 followed by benzoylation of the remaining free hydroxyl group.

  DOI：

  10.1021/jo980735a
• 作为产物：
  描述：

  1,6-anhydro-2-azido-2-deoxy-β-D-galactopyranose 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranose
  参考文献：
  名称：

  Auzanneau, France-Isabelle; Bennis, Khalil; Fanton, Elisabeth, Journal of the Chemical Society. Perkin transactions I, 1998, # 21, p. 3629 - 3635

  摘要：

  DOI：

文献信息

• Auzanneau, France-Isabelle; Bennis, Khalil; Fanton, Elisabeth, Journal of the Chemical Society. Perkin transactions I, 1998, # 21, p. 3629 - 3635
  作者：Auzanneau, France-Isabelle、Bennis, Khalil、Fanton, Elisabeth、Prome, Danielle、Defaye, Jacques、Gelas, Jacques

  DOI：——

  日期：——
• Synthesis of S-Linked Thiooligosaccharide Analogues of Nodulation Factors. 2.¹ Synthesis of an Intermediate Thiotrisaccharide
  作者：France-Isabelle Auzanneau、Monia Mialon、Danielle Promé、Jean-Claude Promé、Jacques Gelas

  DOI：10.1021/jo980735a

  日期：1998.9.1

  An S-linked thiotrisaccharide analogue of chitin that carries different N-protecting groups at the reducing and nonreducing end glucosamine residues was prepared as an intermediate for the synthesis of thioanalogues of nodulation factors. 1,6-Anhydro-2-azido-3-O-benzoyl-2-deoxy-beta-D-glucopyranose (3) was prepared either through the nucleophilic displacement of the 4-triflate galacto analogue 1 with potassium chloroacetate or via the selective acylation of the analogous gluco diol 4. Condensation of 3 with the N-phthalimido trichloroacetimidate 9 led to the disaccharide 10, which was converted in four steps to the glucosyl bromide 15. Nucleophilic displacement of the anomeric bromide by a 4-thiolate derivative of glucosamine (16) bearing a trichloroethoxycarbamate at C-2 was performed in anhydrous oxygen-free THF and led to the desired thiotrisaccharide precursor of thioanalogues of nodulation factors. Alternatively, the disaccharide 10 was prepared by regioselective glycosylation of the 1,6-anhydro diol 4 followed by benzoylation of the remaining free hydroxyl group.