[(2R,3S,4R,5R,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-6-[(2S)-3-oxo-3-phenylmethoxy-2-(2,2,2-trichloroethoxycarbonylamino)propoxy]-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-decanoyloxytetradecanoate | 640291-24-3

• 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: [(2R,3S,4R,5R,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-6-[(2S)-3-oxo-3-phenylmethoxy-2-(2,2,2-trichloroethoxycarbonylamino)propoxy]-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-decanoyloxytetradecanoate
• CAS: 640291-24-3
• 化学式: C₅₂H₈₄Cl₆N₂O₁₄Si
• 分子量: 1202.05
• InChiKey: KXBRDTSWIRAISJ-XBOUISLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.06
• 重原子数：
  75
• 可旋转键数：
  41
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  204
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-6-[(2S)-3-oxo-3-phenylmethoxy-2-(2,2,2-trichloroethoxycarbonylamino)propoxy]-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-decanoyloxytetradecanoate 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  The ‘Ethereal’ nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics

  摘要：

  To overcome the chemical and metabolic instability of the secondary fatty acyl residues in the AGP class of lipid A mimetics, the secondary ether lipid analogs of the potent TLR4 agonist CRX-527 (2) and TLR4 antagonist CRX-526 (3) were synthesized and evaluated along with their ester counterparts for agonist/antagonist activity in both in vitro and in vivo models. Like CRX-527, the secondary ether lipid 4 showed potent agonist activity in both murine and human models. Ether lipid 5, on the other hand, showed potent TLR4 antagonist activity similar to CRX-526 in human cell assays, but did not display any antagonist activity in murine models and, in fact, was weakly agonistic. Glycolipids 2, 4, and 5 were synthesized via a new highly convergent method utilizing a common advanced intermediate strategy. A new method for preparing (R)-3-alkyloxytetradecanoic acids, a key component of ether lipids 4 and 5, is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.060
• 作为产物：
  描述：

  benzyl N-trichloroethoxycarbonyl-O-[6-O-tert-butyldimethylsilyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate 、 (R)-3-decanoyloxytetradecanoic acid 在 4-二甲氨基吡啶 、 二甲基氨基丙基乙基碳酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到[(2R,3S,4R,5R,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-6-[(2S)-3-oxo-3-phenylmethoxy-2-(2,2,2-trichloroethoxycarbonylamino)propoxy]-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-decanoyloxytetradecanoate
  参考文献：
  名称：

  The ‘Ethereal’ nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics

  摘要：

  To overcome the chemical and metabolic instability of the secondary fatty acyl residues in the AGP class of lipid A mimetics, the secondary ether lipid analogs of the potent TLR4 agonist CRX-527 (2) and TLR4 antagonist CRX-526 (3) were synthesized and evaluated along with their ester counterparts for agonist/antagonist activity in both in vitro and in vivo models. Like CRX-527, the secondary ether lipid 4 showed potent agonist activity in both murine and human models. Ether lipid 5, on the other hand, showed potent TLR4 antagonist activity similar to CRX-526 in human cell assays, but did not display any antagonist activity in murine models and, in fact, was weakly agonistic. Glycolipids 2, 4, and 5 were synthesized via a new highly convergent method utilizing a common advanced intermediate strategy. A new method for preparing (R)-3-alkyloxytetradecanoic acids, a key component of ether lipids 4 and 5, is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.060