(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-palmitoylglycerol | 156832-43-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-palmitoylglycerol
• 英文别名: [(2S)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl] hexadecanoate
• CAS: 156832-43-8
• 化学式: C₅₃H₇₂O₉
• 分子量: 853.149
• InChiKey: PUGPHJMCLWQZBO-WOBNBYCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  62
• 可旋转键数：
  33
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-palmitoylglycerol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-palmitoyl-2-O-(tert-butyldimethylsilyl)glycerol
  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 为溶剂， 反应 12.75h， 生成 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-palmitoylglycerol
  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

文献信息

• Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine
  作者：Donald E. Bierer、Larisa G. Dubenko、Joane Litvak、R. Eric Gerber、Judy Chu、Dung L. Thai、Michael S. Tempesta、Thien V. Truong

  DOI：10.1021/jo00128a043

  日期：1995.11

  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.