phenyl-3,4-di-O-benzyl-2,6-di-O-(2,5-difluorobenzoyl)-α-D-thiomannopyranose | 1427066-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-3,4-di-O-benzyl-2,6-di-O-(2,5-difluorobenzoyl)-α-D-thiomannopyranose
• CAS: 1427066-83-8
• 化学式: C₄₀H₃₂F₄O₇S
• 分子量: 732.749
• InChiKey: BSQADLSUQJEXIW-PCOMTGGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.31
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-2,4-di-O-benzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 phenyl-3,4-di-O-benzyl-2,6-di-O-(2,5-difluorobenzoyl)-α-D-thiomannopyranose 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到benzyl [3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-[3,4-di-O-benzyl-2,6-di-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-2,4-di-O-benzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Building Biologics by Chemical Synthesis: Practical Preparation of Di- and Triantennary N-Linked Glycoconjugates

  摘要：

  A unified strategy for the syntheses of bi- and triantennary fully sialylated N-glycans is described. The synthesis capitalizes on a global glycosylation strategy that delivers the desired undeca- and tetradecasaccharide in excellent yields. Finally, conjugation of the glycan to PSMA oligopeptide is described.

  DOI：

  10.1021/ja401385v
• 作为产物：
  描述：

  2,5-二氟苯甲酰氯 、 phenyl-3,4-di-O-benzyl-α-D-thiomannopyranose 在 吡啶 作用下， 反应 4.0h， 以67%的产率得到phenyl-3,4-di-O-benzyl-2,6-di-O-(2,5-difluorobenzoyl)-α-D-thiomannopyranose
  参考文献：
  名称：

  Building Biologics by Chemical Synthesis: Practical Preparation of Di- and Triantennary N-Linked Glycoconjugates

  摘要：

  A unified strategy for the syntheses of bi- and triantennary fully sialylated N-glycans is described. The synthesis capitalizes on a global glycosylation strategy that delivers the desired undeca- and tetradecasaccharide in excellent yields. Finally, conjugation of the glycan to PSMA oligopeptide is described.

  DOI：

  10.1021/ja401385v