methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3-acetyloxy-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-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate | 1415725-04-0

• 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-3-acetyloxy-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-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate
• CAS: 1415725-04-0
• 化学式: C₇₁H₉₃Cl₃N₄O₄₁
• 分子量: 1764.88
• InChiKey: AKIXCPDVNGEUEB-LLEPQOMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  119
• 可旋转键数：
  52
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  572
• 氢给体数：
  4
• 氢受体数：
  42

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3-acetyloxy-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-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-2-yl]methoxy]-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]oxane-2-carboxylate 、 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以73%的产率得到
  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：

  、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3-acetyloxy-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-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-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