[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-3-acetyloxy-2-(acetyloxymethyl)-6-(4-methylphenyl)sulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate | 1360862-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-3-acetyloxy-2-(acetyloxymethyl)-6-(4-methylphenyl)sulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 1360862-19-6
• 化学式: C₅₄H₅₆Cl₃NO₁₄S
• 分子量: 1081.46
• InChiKey: YXYFJVPTTUOACU-SWXILJHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  73
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-3-acetyloxy-2-(acetyloxymethyl)-6-(4-methylphenyl)sulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate 、 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-6-(3-azidopropoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 silver trifluoromethanesulfonate 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以41 %的产率得到methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-5-[(2S,3R,4R,5R,6R)-5-acetyloxy-6-(acetyloxymethyl)-4-[(2R,3R,4S,5S,6R)-3-benzoyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-2-[(2R,3R,4S,5R,6R)-6-(3-azidopropoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  [EN] ANTI-GM1 ANTIBODY BINDING COMPOUNDS
  [FR] COMPOSÉS DE LIAISON À UN ANTICORPS ANTI-GM1

  摘要：

  This disclosure provides glycan-conjugated compounds that specifically bind to anti -GM1 autoantibodies. These glycan-conjugated compounds can include a polymer backbone or support configured to display multiple glycan groups that are designed to mimic the natural GM1 epitope. The glycan-conjugated compounds can also be configured on a solid support. The linked glycan groups can be a novel analogue of the GM1 epitope. When several such glycan groups are configured on a polymeric backbone, the resulting compound provides for potent and specific binding to anti-GM1 IgG and IgM isotype autoantibodies in patient sera. This disclosure thus provides glycan-containing compounds of formula (I) that mimic the natural GM1 epitope, and therapeutically useful polymers that include a multitude of such ligands, designed to bind anti-GM1 antibodiesin vitrofor diagnostic use, and to sequester and eliminate anti-GM1 antibodiesin vivoor extracorporeal (ex vivo) for the treatment anti-GM1 autoantibody related neuropathies.

  公开号：

  WO2022224035A2
• 作为产物：
  描述：

  p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 4-甲基苯硫氯 、 camphor-10-sulfonic acid 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 [(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-3-acetyloxy-2-(acetyloxymethyl)-6-(4-methylphenyl)sulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
  参考文献：
  名称：

  氨基丙基官能化神经节苷脂GM的全合成1个

  摘要：

  GM 1是存在于哺乳动物细胞表面的常见神经节苷脂五糖。已经表明它在细胞通讯和β-淀粉样蛋白聚集的起始中起重要作用。为了合成GM 1，通过[3 + 2]策略开发了有效的合成途径。使用传统的乙酰胺保护的唾液酸基硫糖基供体制备了在还原端带有叠氮丙基的GM 3三糖受体，该化合物的立体选择性比三氯乙酰胺或恶唑烷酮保护的唾液酸供体更好。GM 3轴向4-羟基的糖基化发现二糖供体的β-糖基化高度依赖于供体保护基。带有更刚性的亚苄基的供体给出低的糖基化产率。用乙酸酯取代亚苄基导致有效的偶联和完全保护的GM 1五糖的形成。通过氨基丙基侧链官能化的五糖产生的GM 1的脱保护，这将是生物学研究的宝贵探针。

  DOI：

  10.1007/s11426-011-4449-x