(2R,3S,4R)-1,3,4-tri-O-benzyl-1,2,3,4-undecanetetrol | 164988-61-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4R)-1,3,4-tri-O-benzyl-1,2,3,4-undecanetetrol
• CAS: 164988-61-8
• 化学式: C₃₂H₄₀O₄
• 分子量: 488.667
• InChiKey: SKAJTEHJHQPGLB-IWWXRALLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  36.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1,3,4-tri-O-benzyl-1,2,3,4-undecanetetrol 在 palladium on activated charcoal 、 palladium on barium sulfate 盐酸 、 4 A molecular sieve 、 氢气 、 silver perchlorate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.5h， 生成 1-O-(α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol
  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：

  3,4,5-tri-O-benzyl-D-galactopyranose 在 sodium periodate 、 正丁基锂 作用下， 以 乙醇 、 水 为溶剂， 反应 32.5h， 生成 (2R,3S,4R)-1,3,4-tri-O-benzyl-1,2,3,4-undecanetetrol
  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