3-(benzyloxycarbonylamino)propyl-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-glucopyranose | 933791-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzyloxycarbonylamino)propyl-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-glucopyranose
• CAS: 933791-01-6
• 化学式: C₆₇H₅₇N₃O₁₉
• 分子量: 1208.2
• InChiKey: JRUBAGHESHZSPS-RVCNFTFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  89.0
• 可旋转键数：
  21.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  275.44
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonylamino)propyl-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-glucopyranose 、 在 氰化汞 、 mercury dibromide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 乙硫醇 、 一水合肼 作用下， 以 乙腈 、 四氢呋喃 、 乙醇 为溶剂， 反应 2.33h， 以50%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：

  在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80 mg的产率得到3-(benzyloxycarbonylamino)propyl-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-glucopyranose
  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

文献信息

• Synthesis of five nona-β-(1→6)-d-glucosamines with various patterns of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus
  作者：Olga N. Yudina、Marina L. Gening、Yury E. Tsvetkov、Alexey A. Grachev、Gerald B. Pier、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2011.02.018

  日期：2011.5

  A series of five 3-acetamidopropyl beta-glycosides of nona-beta-(1 -> 6)-glucosamines containing two N-acetyl-glucosamine residues separated by a different number of glucosamine units with free amino groups have been synthesized using a convergent blockwise approach. Oxazoline glycosylation was used to introduce N-acetylglucosamine residues. These nonasaccharides are structurally related to the poly-N-acetylglucosamine (PNAG) extracellular polysaccharide of Staphylococcus aureus and can be used as models for biochemical and immunological studies. (C) 2011 Elsevier Ltd. All rights reserved.