2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside | 211678-02-3

• 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)-6-azido-2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside
• CAS: 211678-02-3
• 化学式: C₅₉H₆₅N₃O₁₂Si
• 分子量: 1036.26
• InChiKey: BRWMBSJEMAMVEY-RMSPJJQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.91
• 重原子数：
  75.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  175.2
• 氢给体数：
  0.0
• 氢受体数：
  13.0

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)-6-azido-2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 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-β-D-galactopyranoside 在 sodium azide 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 39.0h， 生成 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-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

文献信息

• Synthesis of selected aminodeoxy analogues of galabiose and globotriose
  作者：Henrik C. Hansen、Göran Magnusson

  DOI：10.1016/s0008-6215(99)00229-3

  日期：1999.12

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.