Tetracosanoic acid [(1S,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-octyl]-amide | 848827-57-6

• 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: Tetracosanoic acid [(1S,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-octyl]-amide
• CAS: 848827-57-6
• 化学式: C₈₁H₁₁₃NO₉
• 分子量: 1244.79
• InChiKey: AQLYEZRITDKPRH-ORYCFBQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.54
• 重原子数：
  91.0
• 可旋转键数：
  51.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  Tetracosanoic acid [(1S,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-octyl]-amide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 以71%的产率得到(2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-1,3,4-nonanetriol
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027
• 作为产物：
  描述：

  (2S,3S,4R)-2-azido-nonane-1,3,4-triol 在 4 A molecular sieve 吡啶 、 2-氯吡啶 、 二甲基硫 、 三氟甲磺酸酐 、 sodium hydride 、 溶剂黄146 、 1-羟基苯并三唑一水物 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.67h， 生成 Tetracosanoic acid [(1S,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-octyl]-amide
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027