N-((2S,3S,4R)-3,4-dihydroxy-5-propoxy-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)pentan-2-yl)tetracosanamide | 1391851-35-6

• 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: N-((2S,3S,4R)-3,4-dihydroxy-5-propoxy-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)pentan-2-yl)tetracosanamide
• CAS: 1391851-35-6
• 化学式: C₆₆H₉₉NO₁₀
• 分子量: 1066.51
• InChiKey: RHJIJHBAUYIYCH-RSZCCLHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.94
• 重原子数：
  77.0
• 可旋转键数：
  45.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  134.17
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3S,4R)-3,4-dihydroxy-5-propoxy-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)pentan-2-yl)tetracosanamide 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.5h， 以100%的产率得到(2S,3S,4R)-1-O-(α-D-galactosyl)-6-oxa-2-tetracosanoylamino-1,3,4-nonanetriol
  参考文献：
  名称：

  Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

  摘要：

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.025
• 作为产物：
  描述：

  (2R,3R,4R)-1,3,4-trihydroxy-5-propoxypentan-2-yl methanesulfonate 在 盐酸 、 sodium azide 、 四丁基溴化铵 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 92.75h， 生成 N-((2S,3S,4R)-3,4-dihydroxy-5-propoxy-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)pentan-2-yl)tetracosanamide
  参考文献：
  名称：

  Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

  摘要：

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.025