thexyldimethylsilyl 2-O-allyl-3,4-di-O-benzyl-β-D-rhamnopyranoside | 1438257-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thexyldimethylsilyl 2-O-allyl-3,4-di-O-benzyl-β-D-rhamnopyranoside
• 英文别名: 2,3-dimethylbutan-2-yl-dimethyl-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-3-prop-2-enoxyoxan-2-yl]oxysilane
• CAS: 1438257-87-4
• 化学式: C₃₁H₄₆O₅Si
• 分子量: 526.789
• InChiKey: OMAMAEOKPBUOHW-RLIQFMLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,7S)-1,8-bis(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,7-dihydroxyoctanediol 、 thexyldimethylsilyl 2-O-allyl-3,4-di-O-benzyl-β-D-rhamnopyranoside 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以94%的产率得到1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranosyl)-6-O-(thexyldimethylsilyl-3,4-di-O-benzyl-β-D-rhamnopyranosyl)-2-hydroxy-4-hexenediol
  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：

  thexyldimethylsilyl-3,4-di-O-benzylrahmnopyranoside 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到thexyldimethylsilyl 2-O-allyl-3,4-di-O-benzyl-β-D-rhamnopyranoside
  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