methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylate-(2→3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 1400810-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylate-(2→3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• CAS: 1400810-22-1
• 化学式: C₇₂H₇₈Cl₃N₃O₂₅
• 分子量: 1491.78
• InChiKey: MDNVJIDEDNODAB-YEJKIRSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  103.0
• 可旋转键数：
  30.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  340.43
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为产物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylate-(2→3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylate-(2→3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  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