N-((S)-1-((4S,5R)-2,2-dimethyl-5-propyl-1,3-dioxolan-4-yl)-2-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)tetracosanamide | 956103-48-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-((S)-1-((4S,5R)-2,2-dimethyl-5-propyl-1,3-dioxolan-4-yl)-2-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)tetracosanamide
• CAS: 956103-48-3
• 化学式: C₆₈H₁₀₁NO₉
• 分子量: 1076.55
• InChiKey: LIOSJOVZZHRIDR-VGEKJMBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.11
• 重原子数：
  78.0
• 可旋转键数：
  42.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  102.94
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-((S)-1-((4S,5R)-2,2-dimethyl-5-propyl-1,3-dioxolan-4-yl)-2-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)tetracosanamide 在 acid 作用下， 生成
  参考文献：
  名称：

  Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs

  摘要：

  Analogs of immunomodulatory glycolipid OCH (2) were prepared and minimum structure requirement to exhibit equivalent profiles was disclosed. Analogs bearing non-linear hydrocarbon chain in the phytosphingosine moiety (18, 19) were shown for the first time to possess comparable cytokine inducing profile to 2. Molecular modeling of 2/hCD1d complex based on the crystal structure of alpha-GalCer (1)/hCDld complex is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.081
• 作为产物：
  描述：

  2-azido-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3,4-O-isopropylidene-D-ribo-1,3,4-heptanetriol 在 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-((S)-1-((4S,5R)-2,2-dimethyl-5-propyl-1,3-dioxolan-4-yl)-2-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)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