(2S,3S,4R)-1,3,4-tris(phenylmethoxy)icosan-2-amine | 164385-89-1

• 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)-1,3,4-tris(phenylmethoxy)icosan-2-amine
• CAS: 164385-89-1
• 化学式: C₄₁H₆₁NO₃
• 分子量: 615.94
• InChiKey: GEIFCUNVYJMTBI-HMVVSKLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  45
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1,3,4-tris(phenylmethoxy)icosan-2-amine 在 钯 三正丁胺 、 2-氯-1-甲基吡啶碘化物 、 氢气 作用下， 以 四氢呋喃 、 丙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 [(2R)-1-oxo-1-[[(2S,3S,4R)-1,3,4-trihydroxyicosan-2-yl]amino]hexacosan-2-yl] acetate
  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 吡啶 、 正丁基锂 、 sodium azide 、 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 (2S,3S,4R)-1,3,4-tris(phenylmethoxy)icosan-2-amine
  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