1,6-anhydro-2-azido-4-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranose | 1053703-50-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-anhydro-2-azido-4-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-6-[[(1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,4-dibenzoyloxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl benzoate
• CAS: 1053703-50-6
• 化学式: C₄₁H₃₄N₄O₁₃
• 分子量: 790.74
• InChiKey: FSNRSBGDCBQTQY-USFZQVQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  58
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-azido-4-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranose 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 1,6-di-O-acetyl-4-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-2-{[(trichloroethoxy)carbonyl]amino}-α-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-glucopyranose 、 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-D-glucopyranosyl 2,2,2-trichloroacetimidate 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到1,6-anhydro-2-azido-4-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-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

文献信息

• 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.