N-(9-fluorenylmethoxycarbonyl)-O-{β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-[β-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-α-D-galactopyranosyl}-L-threonine | 1219595-28-4

• 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-{β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-[β-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-α-D-galactopyranosyl}-L-threonine
• CAS: 1219595-28-4
• 化学式: C₈₉H₁₃₄N₆O₅₅
• 分子量: 2168.05
• InChiKey: AYLGFKGVTCWEGF-VIDQVFCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -18.68
• 重原子数：
  150.0
• 可旋转键数：
  40.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  931.71
• 氢给体数：
  33.0
• 氢受体数：
  54.0

反应信息

• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-{3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-α-D-galactopyranosyl}-L-threonine 在 二甲基硫 、 三氟甲磺酸 、 间甲酚 、 三氟乙酸 作用下， 反应 4.0h， 以19%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-{β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-[β-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-α-D-galactopyranosyl}-L-threonine
  参考文献：
  名称：

  固相合成带有四-N-乙酰基乳糖胺的核心2十糖的糖肽

  摘要：

  描述了一种新的四糖胺基O-糖氨基酸的合成方法。通过2-三氯乙酰氨基基团辅助的β-糖基化进行乳糖胺基单元的立体选择性组装。由于涉及除去4- O-氯乙酰基的步骤中的低收率，对合成十糖苏氨酸2的初步研究显示出有限的成功。相反，使用（N-苯基）三氟乙酰亚氨酸酯方法通过反复糖基化，由在Gal残基上带有3- O-烯丙基保护基的关键LacNAc衍生物35有效地合成了4- O-苄基化的十糖基苏氨酸50。十糖50用作MUC1相关糖肽的固相合成的基础。合成的糖肽是通过两个酸性过程获得的：在较低的温度下用试剂K从树脂上裂解，然后用低酸度TfOH的稀释混合物进行脱苄基作用。分离了所需的糖肽54作为主要产物，而由于β-GlcNAc糖苷键的酸不稳定特性，产生了一系列缩短糖类的次要产物。

  DOI：

  10.1016/j.tet.2009.12.031