6-azidohexyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside | 652149-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azidohexyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
• CAS: 652149-21-8
• 化学式: C₄₈H₅₆N₄O₁₆
• 分子量: 944.99
• InChiKey: QQWFMIQYTACNJB-BJBRAVCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  68.0
• 可旋转键数：
  23.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  246.72
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  6-azidohexyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.5h， 生成 6-azidohexyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-(2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemo-enzymatic synthesis of tetra-, penta-, and hexasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

  摘要：

  The chemo-enzymatic synthesis is described of beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1--> O(CH2)(6)NH2 (1), beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (2), beta-D-Galp-(1 -->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (3), and beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1--> 3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->O(CH2)(6)NH2 (4), representing fragments of the repeating unit of the Streptococcuspneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk beta-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00292-1
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate 、 6-azidohexyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到6-azidohexyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemo-enzymatic synthesis of tetra-, penta-, and hexasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

  摘要：

  The chemo-enzymatic synthesis is described of beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1--> O(CH2)(6)NH2 (1), beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (2), beta-D-Galp-(1 -->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (3), and beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1--> 3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->O(CH2)(6)NH2 (4), representing fragments of the repeating unit of the Streptococcuspneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk beta-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00292-1