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)-((2-trimethylsilyl)ethyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1400810-20-9

• 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)-((2-trimethylsilyl)ethyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 1400810-20-9
• 化学式: C₇₅H₉₀N₂O₂₅Si
• 分子量: 1447.62
• InChiKey: JUQPMXNVIIPFMR-NJKFRUQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  103.0
• 可旋转键数：
  33.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  316.58
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  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)-((2-trimethylsilyl)ethyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以77.011%的产率得到
  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：

  methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-5-acetyloxy-2-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-6-ethylsulfanyl-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 、 2-(三甲硅基)乙醇 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94%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)-((2-trimethylsilyl)ethyl)-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