benzyl 2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside | 252042-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
• 英文别名: [(3R)-1-[[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-phenylmethoxy-4-(2,2,2-trichloroethoxycarbonyloxy)oxan-3-yl]amino]-1-oxotetradecan-3-yl] tetradecanoate
• CAS: 252042-37-8
• 化学式: C₄₄H₇₂Cl₃NO₁₀
• 分子量: 881.415
• InChiKey: LPMKCZDYHJJPDN-QPXQLFRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  58
• 可旋转键数：
  35
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl chloride 、 benzyl 2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以73%的产率得到benzyl 2-deoxy-6-O-[2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-(2,2,2-trichloroethoxycarbonyl)...
  参考文献：
  名称：

  3-O-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities

  摘要：

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.

  DOI：

  10.1021/jm990222b
• 作为产物：
  描述：

  (R)-3-(dodecanoyloxy)tetradecanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 二甲基氨基丙基乙基碳酰胺 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 benzyl 2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
  参考文献：
  名称：

  3-O-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities

  摘要：

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.

  DOI：

  10.1021/jm990222b

文献信息

• 3-<i>O</i>-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities
  作者：David A. Johnson、David S. Keegan、C. Gregory Sowell、Mark T. Livesay、Craig L. Johnson、Lara M. Taubner、Annalivia Harris、Kent R. Myers、Jennifer D. Thompson、Gary L. Gustafson、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、Yvonne M. Yorgensen、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1021/jm990222b

  日期：1999.11.1

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.