para-tolyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 1410786-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: para-tolyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• 英文别名: p-methylphenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
• CAS: 1410786-12-7
• 化学式: C₂₂H₂₃N₃O₅S
• 分子量: 441.508
• InChiKey: QDKBFEKEOGIIHT-BTOHRNCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102.75
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  para-tolyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 perchloric acid adsorbed on silica gel 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 p-methoxyphenyl (3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Expedient synthesis of two structurally close tetrasaccharides corresponding to the O-antigens of Escherichia coli O127 and Salmonella enterica O13

  摘要：

  Two structurally close tetrasaccharides corresponding to the O-antigens of Escherichia coli O127 and Salmonella enterica O13 have been synthesized using a 'unichemo' approach and minimum number of reaction steps. The yields of all glycosylation steps were excellent with a high stereochemical outcome. A common synthetic strategy has been adopted for the simultaneous synthesis of two tetrasaccharides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.006
• 作为产物：
  描述：

  p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 在 吡啶 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 para-tolyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Expedient synthesis of two structurally close tetrasaccharides corresponding to the O-antigens of Escherichia coli O127 and Salmonella enterica O13

  摘要：

  Two structurally close tetrasaccharides corresponding to the O-antigens of Escherichia coli O127 and Salmonella enterica O13 have been synthesized using a 'unichemo' approach and minimum number of reaction steps. The yields of all glycosylation steps were excellent with a high stereochemical outcome. A common synthetic strategy has been adopted for the simultaneous synthesis of two tetrasaccharides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.006

文献信息

• Expedient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O86 and its conformational analysis
  作者：Ishani Bhaumik、Rajiv Kumar Kar、Anirban Bhunia、Anup Kumar Misra

  DOI：10.1007/s10719-016-9687-x

  日期：2016.12

  Conformational analysis of the synthesized pentasaccharide has been carried out using 2D ROESY NMR spectral analysis and all atom explicit molecular dynamics (MD) simulation technique. Facile synthesis of the pentasaccharide with a 2-aminoethyl linker attached to the reducing end corresponding to the cell wall O-antigen of Escherichia coli O86 strain is reported. Conformational analysis of the synthesized

  报道了具有2-氨基乙基接头的五糖的合成，所述2-氨基乙基接头连接至对应于大肠杆菌O86菌株的细胞壁O-抗原的还原端。合成策略涉及在类似的糖基化反应条件下，对适当保护的单糖中间体进行顺序糖基化。在整个合成策略中，硫代糖苷已被用作糖基供体。已经使用2维ROESY NMR光谱分析和所有原子显式分子动力学（MD）模拟技术对合成的五糖进行了构象分析。 已经报道了具有2-氨基乙基接头的五糖的容易合成，所述2-氨基乙基接头连接到对应于大肠杆菌O86菌株的细胞壁O-抗原的还原端。已经使用2维ROESY NMR光谱分析和所有原子显式分子动力学（MD）模拟技术对合成的五糖进行了构象分析。
• Synthesis of a trisaccharide repeating unit of the O-antigen from Burkholderia cenocepacia and its dimer
  作者：Ningning Bi、Chenghe Xiong、Guoxia Jin、Zhongwu Guo、Guofeng Gu

  DOI：10.1016/j.carres.2017.09.001

  日期：2017.11

  The trisaccharide repeating unit of an O-antigen derived from Burkholderia cenocepacia and its dimer, i.e., α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (1) and α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-(1 → 4)-α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (2), respectively, were synthesized via a highly convergent strategy. Glycosylation of galactosaminyl acceptor

  源自洋葱伯克霍尔德菌的O抗原的三糖重复单元及其二聚体，即α-L-Rhap-（1→3）-α-D-GalpNAc-（1→3）-β-D-GalpNAc-O （CH2）3N3（1）和α-L-Rhap-（1→3）-α-D-GalpNAc-（1→3）-β-D-GalpNAc-（1→4）-α-L-Rhap-通过高度收敛的策略分别合成了（1→3）-α-D-GalpNAc-（1→3）-β-D-GalpNAc-O（ ）3N3（2）。将半乳糖胺基受体4与半乳糖胺基三氯乙酸亚氨酸酯供体5进行糖基化，然后使所得的二糖受体12与鼠李糖亚氨酸酯供体6缩合，以提供立体选择性的三糖基硫代糖苷3，其用作构建1和2的关键和常见糖基供体。标题分子1是通过将3-叠氮丙醇与3进行糖基化并随后进行整体脱保护而制备的，