methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2S,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2-methoxycarbonyloxan-2-yl]oxy-6-[(2R,3S,4S,5R,6R)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-3-phenylmethoxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate | 1415725-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2S,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2-methoxycarbonyloxan-2-yl]oxy-6-[(2R,3S,4S,5R,6R)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-3-phenylmethoxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate
• CAS: 1415725-02-8
• 化学式: C₇₉H₁₀₉N₃O₄₀Si
• 分子量: 1768.82
• InChiKey: GKIMQTHBDHAQBS-COVNSJGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  123
• 可旋转键数：
  55
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  531
• 氢给体数：
  3
• 氢受体数：
  40

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2S,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2-methoxycarbonyloxan-2-yl]oxy-6-[(2R,3S,4S,5R,6R)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-3-phenylmethoxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  First Synthesis of a Pentasaccharide Moiety of Ganglioside GAA-7 Containing Unusually Modified Sialic Acids through the Use of N-Troc-sialic Acid Derivative as a Key Unit

  摘要：

  The pentasaccharide part of the potent neuritogenic ganglioside GAA-7 has been synthesized for the first time. The unique branched terminus constituting partially modified sialic acids and N-acetylgalactosamine was successfully established by stereoselective double-sialylation using 8-O-methyl-N-Troc-sialic acid as a donor. The final 4 + 1 coupling reaction provided a high yield of pentasaccharide, which was deprotected to deliver the target molecule.

  DOI：

  10.1021/ol303122w
• 作为产物：
  描述：

  、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以95%的产率得到methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2S,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2-methoxycarbonyloxan-2-yl]oxy-6-[(2R,3S,4S,5R,6R)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-3-phenylmethoxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  First Synthesis of a Pentasaccharide Moiety of Ganglioside GAA-7 Containing Unusually Modified Sialic Acids through the Use of N-Troc-sialic Acid Derivative as a Key Unit

  摘要：

  The pentasaccharide part of the potent neuritogenic ganglioside GAA-7 has been synthesized for the first time. The unique branched terminus constituting partially modified sialic acids and N-acetylgalactosamine was successfully established by stereoselective double-sialylation using 8-O-methyl-N-Troc-sialic acid as a donor. The final 4 + 1 coupling reaction provided a high yield of pentasaccharide, which was deprotected to deliver the target molecule.

  DOI：

  10.1021/ol303122w