methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1R,2R)-1,3-diacetyloxy-2-hydroxypropyl]-2-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxane-2-carboxylate | 1415724-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1R,2R)-1,3-diacetyloxy-2-hydroxypropyl]-2-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxane-2-carboxylate
• CAS: 1415724-81-0
• 化学式: C₂₅H₃₀Cl₃NO₁₂S
• 分子量: 674.938
• InChiKey: QZOFAXMEXSXWAR-IPSPCLKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  198
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1R,2R)-1,3-diacetyloxy-2-hydroxypropyl]-2-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxane-2-carboxylate 在 溶剂黄146 、 三乙胺 、 锌 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.5h， 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：

  在 4-二甲氨基吡啶 、 1-selenocarbamoylpiperidine 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1R,2R)-1,3-diacetyloxy-2-hydroxypropyl]-2-phenylsulfanyl-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