2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside | 211678-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside
• CAS: 211678-04-5
• 化学式: C₆₆H₇₂O₁₅SSi
• 分子量: 1165.44
• InChiKey: IDEPMEBBYMMTSW-ROSQKUIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.31
• 重原子数：
  83.0
• 可旋转键数：
  27.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-6-O-tosyl-β-D-galactopyranoside 在 palladium on activated charcoal 盐酸 、 sodium azide 、 15-冠醚-5 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 Gal(a1-4)Gal6N(b)-O-EtTMS
  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-β-D-galactopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 34.0h， 生成 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-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