ethyl 6-O-(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 | 932015-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-(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
• 英文别名: [(2R,3S,4R,5R,6R)-4-benzoyloxy-6-[[(2R,3S,4R,5R,6S)-3,4-dibenzoyloxy-5-(1,3-dioxoisoindol-2-yl)-6-ethylsulfanyloxan-2-yl]methoxy]-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 932015-07-1
• 化学式: C₅₈H₄₈N₂O₁₆S
• 分子量: 1061.09
• InChiKey: WQLOUYXDGVEGLG-CSBITOINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  77
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  253
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-(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 溴 、 氰化汞 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.33h， 生成
  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 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 ethyl 6-O-(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
  参考文献：
  名称：

  Synthesis of β-(1→6)-linked glucosamine oligosaccharides corresponding to fragments of the bacterial surface polysaccharide poly-N-acetylglucosamine

  摘要：

  A series of 3-beta-acetamidopropyl oligo-beta-(1 -> 6)-glucosamines consisting of 5, 7, 9 and 11 glucosamine residues, and a series of corresponding per-N-acetylated derivatives were synthesized using a convergent blockwise approach. These compounds represent fragments of a bacterial surface polysaccharide produced by numerous bacterial pathogens, including Staphylococcus aureus, and will be used as models for its biochemical and immunological properties. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.010

文献信息

• Synthesis, NMR, and Conformational Studies of Cyclic Oligo-(1→6)-β-D-Glucosamines
  作者：Marina L. Gening、Denis V. Titov、Alexey A. Grachev、Alexey G. Gerbst、Olga N. Yudina、Alexander S. Shashkov、Alexander O. Chizhov、Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1002/ejoc.200901275

  日期：2010.5

  2-N-phthaloyl group to control β-glycosylation. Both phenomena may be accounted for by conformational features of the linear bifunctional precursors. According to computer modeling and NMR conformational studies, the described linear (1→6)-β-linked oligoglucosamines exist in a right-handed helix-like conformation, in which the glycosyl donor and acceptor moieties are prearranged in a way that facilitates

  首次合成了一系列同源环状低聚糖-(1→6)-β-D-葡糖胺，由 2 到 7 个残基组成，代表了一种新型的功能化环状低聚糖。无论无环前体的长度如何，所研究的大环化反应的产率都非常高。对于由四到七个葡糖胺单元构成的化合物，尽管存在强烈参与的 2-N-邻苯二甲酰基以控制 β-糖基化，但作为副产物形成的 α-立体异构体。这两种现象都可以通过线性双功能前体的构象特征来解释。根据计算机建模和 NMR 构象研究，所描述的线性 (1→6)-β-连接的低聚葡萄糖胺以右手螺旋状构象存在，其中糖基供体和受体部分以促进α-侧分子内糖基化的方式预先排列。制备的环低聚葡糖胺的构象灵活性不同，如它们的光谱特征和计算的非球面分布所示。此外，所获得的化合物不具有明显的疏水腔，这与众所周知的环糊精相反。所有这些特性为使用这些新型环状寡糖作为构建生物分子偶联物的支架提供了极好的基础。如它们的光谱特性和计算出的非球面分布所示。此
• 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.