[(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 | 1415724-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(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
• CAS: 1415724-90-1
• 化学式: C₃₈H₄₇N₃O₁₁Si
• 分子量: 749.89
• InChiKey: WMJIEBZTXJXCMP-JUDLNMNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  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 、 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 以10%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：

  在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到[(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
  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