N-methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonamide | 1021159-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonamide
• CAS: 1021159-66-9
• 化学式: C₂₀H₃₀N₂O₁₂
• 分子量: 490.464
• InChiKey: QNSMIAHAHJLZTR-DCDDNHAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  192.86
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  二乙基亚磷酰氯 、 N-methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以85%的产率得到(N-methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonamide) 2-O-(diethyl phosphite)
  参考文献：
  名称：

  Efficient Synthesis of MUC4 Sialylglycopeptide through the New Sialylation Using 5-Acetamido-Neuraminamide Donors

  摘要：

  Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy2-O-beta-D-glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-l-amide-2-phosphite) derivatives, and the synthesis of the sialyl-T-N-MUC4 glycopeptide are described. The sialylation was performed in CH2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated alpha-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-alpha(2,6)-GalN(3) was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-T-N serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-T-N serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-T-N-MUC4 glycopeptide.

  DOI：

  10.1021/jo702609p
• 作为产物：
  描述：

  在 高氯酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.5h， 生成 N-methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonamide
  参考文献：
  名称：

  Efficient Synthesis of MUC4 Sialylglycopeptide through the New Sialylation Using 5-Acetamido-Neuraminamide Donors

  摘要：

  Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy2-O-beta-D-glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-l-amide-2-phosphite) derivatives, and the synthesis of the sialyl-T-N-MUC4 glycopeptide are described. The sialylation was performed in CH2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated alpha-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-alpha(2,6)-GalN(3) was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-T-N serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-T-N serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-T-N-MUC4 glycopeptide.

  DOI：

  10.1021/jo702609p