2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside | 211677-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside
• CAS: 211677-99-5
• 化学式: C₃₂H₃₈O₁₀SSi
• 分子量: 642.799
• InChiKey: QLVDIEMCPZUKPA-XSCYCRSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside 在 sodium azide 、 15-冠醚-5 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 96.0h， 生成 (2R,3R,4R,5R,6R)-6-Azidomethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapGJ96 from Escherichia coli

  摘要：

  The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2-(trimethylsilyl)ethyl (alpha-D-galactopyranosyl)-(1-->4)-beta-D-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K-rel; relative to the reference inhibitor) were: 157, 13, and < 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00020-2
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 在 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 23.5h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapGJ96 from Escherichia coli

  摘要：

  The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2-(trimethylsilyl)ethyl (alpha-D-galactopyranosyl)-(1-->4)-beta-D-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K-rel; relative to the reference inhibitor) were: 157, 13, and < 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00020-2