[(2S,3S,4R)-2-[[(2R)-2-acetyloxyhexacosanoyl]amino]-3-benzoyloxy-1-hydroxyicosan-4-yl] benzoate | 164989-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3S,4R)-2-[[(2R)-2-acetyloxyhexacosanoyl]amino]-3-benzoyloxy-1-hydroxyicosan-4-yl] benzoate
• CAS: 164989-17-7
• 化学式: C₆₂H₁₀₃NO₈
• 分子量: 990.502
• InChiKey: JAVDXSVRHUKKLX-ITARLHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23
• 重原子数：
  71
• 可旋转键数：
  51
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride 、 [(2S,3S,4R)-2-[[(2R)-2-acetyloxyhexacosanoyl]amino]-3-benzoyloxy-1-hydroxyicosan-4-yl] benzoate 在 4 A molecular sieve 、 silver perchlorate 、 tin(ll) chloride 作用下， 生成 [(2S,3S,4R)-2-[[(2R)-2-acetyloxyhexacosanoyl]amino]-3-benzoyloxy-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyicosan-4-yl] benzoate
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018
• 作为产物：
  描述：

  溴代十五烷 在 palladium on activated charcoal 、 钯 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 sodium azide 、 三正丁胺 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 113.0h， 生成 [(2S,3S,4R)-2-[[(2R)-2-acetyloxyhexacosanoyl]amino]-3-benzoyloxy-1-hydroxyicosan-4-yl] benzoate
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018