benzyl [3,6-di-O-benzyl-2,4-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-2-O-benzyl-4,6-O-(R)-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-Dglucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1400810-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl [3,6-di-O-benzyl-2,4-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-2-O-benzyl-4,6-O-(R)-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-Dglucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 1400810-14-1
• 化学式: C₁₁₇H₁₀₄F₄N₂O₂₅
• 分子量: 2014.1
• InChiKey: WPZUQIZMFZHEEI-GZKZQTOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.7
• 重原子数：
  148.0
• 可旋转键数：
  40.0
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  284.27
• 氢给体数：
  0.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  benzyl [3,6-di-O-benzyl-2,4-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-2-O-benzyl-4,6-O-(R)-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-Dglucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 硼烷四氢呋喃络合物 、 di-n-butylboron triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以88%的产率得到benzyl [3,6-di-O-benzyl-2,4-di-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
  参考文献：
  名称：

  Solving the Convergence Problem in the Synthesis of Triantennary N-Glycan Relevant to Prostate-Specific Membrane Antigen (PSMA)

  摘要：

  The first total synthesis of triantennary, fully sialylated N-glycan of complex type is described. Two strategies for installation of sialylated antennae are explored, and both approaches converge on a global glycosylation step that delivers the desired tetradecasaccharide in good yields.

  DOI：

  10.1021/ja307628w
• 作为产物：
  描述：

  benzyl 2-O-benzyl-4,6-O-(R)-benzylidene-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 、 thiophenyl 3,6-di-O-benzyl-2,4-di-O-(2,5-difluorobenzoyl)-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 以90%的产率得到benzyl [3,6-di-O-benzyl-2,4-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-2-O-benzyl-4,6-O-(R)-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-Dglucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Solving the Convergence Problem in the Synthesis of Triantennary N-Glycan Relevant to Prostate-Specific Membrane Antigen (PSMA)

  摘要：

  The first total synthesis of triantennary, fully sialylated N-glycan of complex type is described. Two strategies for installation of sialylated antennae are explored, and both approaches converge on a global glycosylation step that delivers the desired tetradecasaccharide in good yields.

  DOI：

  10.1021/ja307628w