(R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,4aR,7R,8R,8aS)-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester | 331475-42-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,4aR,7R,8R,8aS)-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• 英文别名: [(2R,4aR,7R,8R,8aS)-2-phenyl-6-(2,2,2-trichloroethanimidoyl)oxy-7-(2,2,2-trichloroethoxycarbonylamino)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 331475-42-4
• 化学式: C₄₆H₇₀Cl₆N₂O₁₀
• 分子量: 1023.79
• InChiKey: AEZKMEXRKUGCLQ-PRNLBJEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  64
• 可旋转键数：
  34
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 、 (R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,4aR,7R,8R,8aS)-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到
  参考文献：
  名称：

  Synthesis and bioactivity of fluorescence- and biotin-labeled lipid A analogues for investigation of recognition mechanism in innate immunity

  摘要：

  Fluorescence- and biotin-labeled lipid A analogues were synthesized for the investigation of bacterial lipopolysaccharide (LPS)/lipid A recognition in the innate immune system. For the introduction of the labeling moiety, a hydrophilic glutaryl-glucose linker was used for maintaining the bioactivity and also for preventing self-aggregation, which causes quenching of the fluorescence. We also observed the biological activity of the labeled compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.041
• 作为产物：
  描述：

  三氯乙腈 、 2-deoxy-4,6-di-O-benzylidene-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 Dowex 1-X₈ (OH^- form) in MicroKan 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到(R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,4aR,7R,8R,8aS)-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  First Total Synthesis of the Re-Type Lipopolysaccharide

  摘要：

  Three sequential efficient glycosylation reactions starting from D-glucosamine were used in the first total synthesis of Escherichia coli Re lipopolysaccharide, which is one of the most simple lipopolysaccharides found on the surface of living bacteria.

  DOI：

  10.1002/1521-3773(20010417)40:8<1475::aid-anie1475>3.0.co;2-v