| 1415724-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1415724-95-6
• 化学式: C₇₈H₉₉Cl₆N₅O₃₅Si
• 分子量: 1907.46
• InChiKey: NXQHPTHSHLKDHN-LWBMHQLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.31
• 重原子数：
  125.0
• 可旋转键数：
  38.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  482.11
• 氢给体数：
  2.0
• 氢受体数：
  36.0

反应信息

• 作为产物：
  描述：

  [(2S,4aR,6R,7R,8S,8aS)-8-[(2S,3R,4R,5R,6R)-3-azido-4-hydroxy-6-(hydroxymethyl)-5-phenylmethoxyoxan-2-yl]oxy-2-phenyl-6-(2-trimethylsilylethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate 、 methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxane-2-carboxylate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 反应 2.0h， 生成 methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-6-[[(2S,4aR,6R,7R,8S,8aS)-7-benzoyloxy-2-phenyl-6-(2-trimethylsilylethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-5-azido-4-hydroxy-3-phenylmethoxyoxan-2-yl]methoxy]-4-acetyloxy-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-5-(2,2,2-trichloroethoxycarbonylamino)oxane-2-carboxylate 、 methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-6-[[(2S,4aR,6R,7R,8S,8aS)-7-benzoyloxy-2-phenyl-6-(2-trimethylsilylethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4-[(2S,4S,5R,6R)-4-acetyloxy-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2-methoxycarbonyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-5-azido-3-phenylmethoxyoxan-2-yl]methoxy]-4-acetyloxy-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-5-(2,2,2-trichloroethoxycarbonylamino)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