1-O-(ammonium (Z)-neryl phosphoryl)-β-D-arabinofuranose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-O-(ammonium (Z)-neryl phosphoryl)-β-D-arabinofuranose
• 英文别名: azane;[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl] [(2Z)-3,7-dimethylocta-2,6-dienyl] hydrogen phosphate
• 化学式: C₁₅H₂₇O₈P*H₃N
• 分子量: 383.379
• InChiKey: YVYCVSPZXDHXKV-DCJMGKPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  橙花醇 、 bis(triethylammonium) (2,3,5-tri-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl) phosphate 在 吡啶 、 三氯乙腈 、 氟化铵 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以76%的产率得到1-O-(ammonium (Z)-neryl phosphoryl)-β-D-arabinofuranose
  参考文献：
  名称：

  Synthesis of Lipid-Linked Arabinofuranose Donors for Glycosyltransferases

  摘要：

  Mycobacteria and corynebacteria use decaprenylphosphoryl-beta-D-arabinofuranose (DPA) as a critical cell wall building block. Arabinofuranosyltransferases that process this substrate to mediate cell wall assembly have served as drug targets, but little is known about the substrate specificity of any of these enzymes. To probe substrate recognition of DPA, we developed a general and efficient synthetic route to beta-D-arabinofuranosyl phosphodiesters. In this approach, the key glycosyl phosphodiester bond-forming reaction proceeds with high beta-selectivity In addition to its stereoselectivity, our route provides the means to readily access a variety of different lipid analogues, including aliphatic and polyprenyl substrates.

  DOI：

  10.1021/jo302507p