N-9-fluorenylmethoxycarbonyl O-[methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonoate]-(2->6)-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-serine | 1021159-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-9-fluorenylmethoxycarbonyl O-[methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonoate]-(2->6)-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-serine
• CAS: 1021159-78-3
• 化学式: C₃₈H₄₉N₃O₁₈
• 分子量: 835.816
• InChiKey: XQJMPSMMPFMOIV-QDNYZSMTSA-N

反应信息

• 作为产物：
  描述：

  、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 苯甲醚 、 三氟乙酸 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 3.5h， 以53 mg的产率得到N-9-fluorenylmethoxycarbonyl O-[methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonoate]-(2->6)-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-serine
  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