6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide | 933790-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide
• CAS: 933790-98-8
• 化学式: C₅₆H₄₃BrN₂O₁₆
• 分子量: 1079.87
• InChiKey: POARIUMLHNCBID-UFLLXTOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  75.0
• 可旋转键数：
  14.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  227.88
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 、 3-(Fmoc-氨基)-1-丙醇 在 氰化汞 、 mercury dibromide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以30%的产率得到
  参考文献：
  名称：

  The study of the reaction of terminated oligomerization in the synthesis of oligo-(β1-6)-glucosamines

  摘要：

  The applicability of terminated oligomerization to the synthesis of oligo-(beta 1-6)-glucosamines, fragments of the intercellular polysaccharide adhesin of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and spacered mono- and disaccharides as terminating molecules were also attempted. The primary formation of cyclic products of monomer intramolecular glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approximately 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligoglucosamines with a high molecular mass.

  DOI：

  10.1134/s1068162006040108
• 作为产物：
  描述：

  ethyl 6-O-(6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 甲醇 、 溴 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide
  参考文献：
  名称：

  The study of the reaction of terminated oligomerization in the synthesis of oligo-(β1-6)-glucosamines

  摘要：

  The applicability of terminated oligomerization to the synthesis of oligo-(beta 1-6)-glucosamines, fragments of the intercellular polysaccharide adhesin of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and spacered mono- and disaccharides as terminating molecules were also attempted. The primary formation of cyclic products of monomer intramolecular glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approximately 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligoglucosamines with a high molecular mass.

  DOI：

  10.1134/s1068162006040108