(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 211678-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 211678-09-0
• 化学式: C₆₀H₇₀O₁₂Si
• 分子量: 1011.29
• InChiKey: QTJAZEBHGGKWHQ-MFGHCHBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.49
• 重原子数：
  73.0
• 可旋转键数：
  26.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  118.6
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (2S,3R,4R,5R,6R)-4,5-Dihydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid
  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-benzyl-β-D-galactopyranoside 在 sodium hypochlorite 、 N-碘代丁二酰亚胺 、 2,2,6,6-四甲基哌啶氧化物 、 三氟甲磺酸 、 4 A molecular sieve 、 四丁基溴化铵 、 碳酸氢钠 、 sodium chloride 、 potassium bromide 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  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