2-azido-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecanol | 164989-45-1

• 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: 2-azido-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecanol
• 英文别名: (2S,3R,4S,5S,6R)-2-(2-azidooctadecoxy)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 164989-45-1
• 化学式: C₅₂H₇₁N₃O₆
• 分子量: 834.152
• InChiKey: HBBMPLXHTHTMQY-ZXXUPBDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  61
• 可旋转键数：
  32
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-azido-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecanol 在 palladium on activated charcoal 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 1-O-(2,3,4,6-tetra-O-benzyl-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：

  n-溴代已基三苯基膦 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 4 A molecular sieve 、 氢气 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 2-azido-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)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

文献信息

• Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice
  作者：Masahiro Morita、Kazuhiro Motoki、Kohji Akimoto、Takenori Natori、Teruyuki Sakai、Eiji Sawa、Kazuo Yamaji、Yasuhiko Koezuka、Eiichi Kobayashi、Hideaki Fukushima

  DOI：10.1021/jm00012a018

  日期：1995.6

  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.