methyl 6-O-cyclopentyl-2,3-di-O-tetradecyl-α-D-glucopyranoside | 1115270-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-cyclopentyl-2,3-di-O-tetradecyl-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(cyclopentyloxymethyl)-6-methoxy-4,5-di(tetradecoxy)oxan-3-ol
• CAS: 1115270-62-6
• 化学式: C₄₀H₇₈O₆
• 分子量: 655.056
• InChiKey: TYVANODGZIFRHX-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  46
• 可旋转键数：
  32
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 6-O-cyclopentyl-4-O-(4'-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到methyl 6-O-cyclopentyl-2,3-di-O-tetradecyl-α-D-glucopyranoside
  参考文献：
  名称：

  Glycolipids and Benzylammonium Lipids as Novel Antisepsis Agents: Synthesis and Biological Characterization

  摘要：

  New glycolipids and a benzylammonium lipid were rationally designed by varying the chemical structure of a D-glucose-derived hit compound active as lipid A antagonist. We report the synthesis of these compounds, their in vitro activity as lipid A antagonists on HEK cells, and the capacity to inhibit LPS-induced septic shock in vivo. The lack of toxicity and the good in vivo activity suggest the use of some compounds of the panel as hits for antisepsis drug development.

  DOI：

  10.1021/jm801333m

文献信息

• Glycolipids and Benzylammonium Lipids as Novel Antisepsis Agents: Synthesis and Biological Characterization
  作者：Matteo Piazza、Clara Rossini、Silvia Della Fiorentina、Chiara Pozzi、Francesca Comelli、Isabella Bettoni、Paola Fusi、Barbara Costa、Francesco Peri

  DOI：10.1021/jm801333m

  日期：2009.2.26

  New glycolipids and a benzylammonium lipid were rationally designed by varying the chemical structure of a D-glucose-derived hit compound active as lipid A antagonist. We report the synthesis of these compounds, their in vitro activity as lipid A antagonists on HEK cells, and the capacity to inhibit LPS-induced septic shock in vivo. The lack of toxicity and the good in vivo activity suggest the use of some compounds of the panel as hits for antisepsis drug development.