(2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol | 156832-54-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol
• 英文别名: [(2R)-2-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 156832-54-1
• 化学式: C₅₈H₈₄NO₁₂P
• 分子量: 1018.28
• InChiKey: VHBLYJSLTIELIY-GRAHYALFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  72
• 可旋转键数：
  39
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 43.0h， 以76.6%的产率得到(2R)-β-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol
  参考文献：
  名称：

  Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine

  摘要：

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

  DOI：

  10.1021/jo00128a043
• 作为产物：
  描述：

  棕榈酸酐 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 42.0h， 生成 (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol
  参考文献：
  名称：

  Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine

  摘要：

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

  DOI：

  10.1021/jo00128a043