2-(trimethylsilyl)ethyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-glucopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy->-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl->-L-rhamnopyranoside | 1384245-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-glucopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy->-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl->-L-rhamnopyranoside
• CAS: 1384245-05-9
• 化学式: C₇₂H₈₇NO₁₉Si
• 分子量: 1298.56
• InChiKey: SMWYLJPCFNPMSB-DSVNJXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  93.0
• 可旋转键数：
  31.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  218.76
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-glucopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy->-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl->-L-rhamnopyranoside 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 以57%的产率得到2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthetic Oligosaccharides as Tools to Demonstrate Cross-Reactivity between Polysaccharide Antigens

  摘要：

  Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colt:is, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide of this bacterium is considered both;l virulence factor and a protective antigen. It is built up of the linear tetrasaccharide repeating unit [3)-alpha-L-Rhap-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-GlcNAcp-(1 -> 3)-alpha-L-Rhap-(1 ->] differing from that of the O-SP of Shigella dysenteriae type 1 (SD) only in that the latter contains a D-Galp residue in place of the glucose moiety of the former. The close similarity of the O-SPs of these bacteria indicated a possible cross-reactivity, To answer this question we synthesized several oligosaccharide fragments of E. coli 0148 O-SP, up to a dodecasaccharide, as well as their bovine serum albumin or recombinant diphtheria toxin conjugates. Immunization of mice with these conjugates induced anti-O-SP-specific serum IgG antibody responses. The antisera reacted equally well with the LPSs of both bacteria, indicating cross-reactivity between the SD and E. coli 0148 O-SPs that was further supported by Western-blot and dot-blot analyses, as well as by inhibition of binding between the antisera and the O-SPs of both bacteria.

  DOI：

  10.1021/jo300299p
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-glucopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 、 乙酸酐 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 23.0 ℃ 、1.38 MPa 条件下， 反应 1.0h， 生成 2-(trimethylsilyl)ethyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-glucopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy->-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl->-L-rhamnopyranoside
  参考文献：
  名称：

  Synthetic Oligosaccharides as Tools to Demonstrate Cross-Reactivity between Polysaccharide Antigens

  摘要：

  Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colt:is, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide of this bacterium is considered both;l virulence factor and a protective antigen. It is built up of the linear tetrasaccharide repeating unit [3)-alpha-L-Rhap-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-GlcNAcp-(1 -> 3)-alpha-L-Rhap-(1 ->] differing from that of the O-SP of Shigella dysenteriae type 1 (SD) only in that the latter contains a D-Galp residue in place of the glucose moiety of the former. The close similarity of the O-SPs of these bacteria indicated a possible cross-reactivity, To answer this question we synthesized several oligosaccharide fragments of E. coli 0148 O-SP, up to a dodecasaccharide, as well as their bovine serum albumin or recombinant diphtheria toxin conjugates. Immunization of mice with these conjugates induced anti-O-SP-specific serum IgG antibody responses. The antisera reacted equally well with the LPSs of both bacteria, indicating cross-reactivity between the SD and E. coli 0148 O-SPs that was further supported by Western-blot and dot-blot analyses, as well as by inhibition of binding between the antisera and the O-SPs of both bacteria.

  DOI：

  10.1021/jo300299p