allyl 2-deoxy-4-O-diphenylphosphono-6-O-methyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside | 214051-06-6

• 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: allyl 2-deoxy-4-O-diphenylphosphono-6-O-methyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3-diphenoxyphosphoryloxy-2-(methoxymethyl)-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 214051-06-6
• 化学式: C₅₃H₈₁Cl₃NO₁₃P
• 分子量: 1077.56
• InChiKey: LURMIIJVEVEMAP-RKMGHAFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  71
• 可旋转键数：
  42
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  allyl 2-deoxy-4-O-diphenylphosphono-6-O-methyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 (R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-2-methoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives

  摘要：

  The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00326-2
• 作为产物：
  描述：

  trimethoxonium tetrafluoroborate 、 allyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到allyl 2-deoxy-4-O-diphenylphosphono-6-O-methyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives

  摘要：

  The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00326-2

文献信息

• Lipid A-Type Pyrancarboxylic Acid Derivatives, their Synthesis and their Biological Activities
  作者：Takashi Mochizuki、Yuji Iwano、Masao Shiozaki、Shin-ichi Kurakata、Saori Kanai、Masahiro Nishijima

  DOI：10.1016/s0040-4020(00)00684-0

  日期：2000.9

  Synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing sugar part of the disaccharide instead of the phosphoric acid group in lipid A, is described. We investigated the influence of the substituents in the 2'- and 6'-position of the molecules synthesized on their activities toward human monoblastic U937 cells. It was revealed that a series of compounds, possessing an acetamido group in the 2'-position showed strong LPS-antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.