2-{methyl-O-[2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl]}-5-{methyl[methyl 2,3,4-tri-O-benzyl-α-D-xylopyranosyl]}-3-(phenylselenyl)tetrahydrofuran | 1395881-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{methyl-O-[2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl]}-5-{methyl[methyl 2,3,4-tri-O-benzyl-α-D-xylopyranosyl]}-3-(phenylselenyl)tetrahydrofuran
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-[[(2S,4R,5S)-4-phenylselanyl-5-[[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]methyl]oxane
• CAS: 1395881-35-2
• 化学式: C₇₃H₇₈O₁₂Se
• 分子量: 1226.38
• InChiKey: FMWMUPCRNGHNHO-GGNBRJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.19
• 重原子数：
  86
• 可旋转键数：
  30
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-{methyl-O-[2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl]}-5-{methyl[methyl 2,3,4-tri-O-benzyl-α-D-xylopyranosyl]}-3-(phenylselenyl)tetrahydrofuran 在 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.0h， 以96%的产率得到(2R,5S)-2-{methyl-O-[2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl]}-5-{methyl[methyl 2,3,4-tri-O-benzyl-α-D-xylopyranosyl]}-2H,5H-dihydrofuran
  参考文献：
  名称：

  Synthesis of a Structural Analogue of the Repeating Unit from Streptococcus pneumoniae 19F Capsular Polysaccharide Based on the Cross-Metathesis–Selenocyclization Reaction Sequence

  摘要：

  Pseudo-oligosaccharides have attracted much interest as scaffolds for the synthesis of sugar mimics endowed with very similar biological properties but structurally and synthetically simpler than their natural counterparts. Herein, the synthesis of pseudo-oligosaccharides using the cross-metathesis reaction between distinct sugar-olefins followed by intramolecular selenocyclization of the obtained heterodimer as key steps is first investigated. This methodology has been then applied to the preparation of structural analogues of the trisaccharide repeating unit from Streptococcus pneumoniae 19F. The inhibition abilities of the synthetic molecules were evaluated by a competitive ELISA assay using a rabbit polyclonal anti-19F serum.

  DOI：

  10.1021/jo4001146
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以242 mg的产率得到2-{methyl-O-[2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl]}-5-{methyl[methyl 2,3,4-tri-O-benzyl-α-D-xylopyranosyl]}-3-(phenylselenyl)tetrahydrofuran
  参考文献：
  名称：

  Synthesis of a Structural Analogue of the Repeating Unit from Streptococcus pneumoniae 19F Capsular Polysaccharide Based on the Cross-Metathesis–Selenocyclization Reaction Sequence

  摘要：

  Pseudo-oligosaccharides have attracted much interest as scaffolds for the synthesis of sugar mimics endowed with very similar biological properties but structurally and synthetically simpler than their natural counterparts. Herein, the synthesis of pseudo-oligosaccharides using the cross-metathesis reaction between distinct sugar-olefins followed by intramolecular selenocyclization of the obtained heterodimer as key steps is first investigated. This methodology has been then applied to the preparation of structural analogues of the trisaccharide repeating unit from Streptococcus pneumoniae 19F. The inhibition abilities of the synthetic molecules were evaluated by a competitive ELISA assay using a rabbit polyclonal anti-19F serum.

  DOI：

  10.1021/jo4001146

文献信息

• Synthesis of a Structural Analogue of the Repeating Unit from <i>Streptococcus pneumoniae</i> 19F Capsular Polysaccharide Based on the Cross-Metathesis–Selenocyclization Reaction Sequence
  作者：Paolo Ronchi、Catalina Scarponi、Matteo Salvi、Silvia Fallarini、Laura Polito、Enrico Caneva、Luana Bagnoli、Luigi Lay

  DOI：10.1021/jo4001146

  日期：2013.6.7

  Pseudo-oligosaccharides have attracted much interest as scaffolds for the synthesis of sugar mimics endowed with very similar biological properties but structurally and synthetically simpler than their natural counterparts. Herein, the synthesis of pseudo-oligosaccharides using the cross-metathesis reaction between distinct sugar-olefins followed by intramolecular selenocyclization of the obtained heterodimer as key steps is first investigated. This methodology has been then applied to the preparation of structural analogues of the trisaccharide repeating unit from Streptococcus pneumoniae 19F. The inhibition abilities of the synthetic molecules were evaluated by a competitive ELISA assay using a rabbit polyclonal anti-19F serum.