5-[O-(2l,3l,4l,6l-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-[N-(uracil-6-carboximido)]-2,2-dimethyl-1,3-dioxane | 1400872-59-4

• 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: 5-[O-(2l,3l,4l,6l-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-[N-(uracil-6-carboximido)]-2,2-dimethyl-1,3-dioxane
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[5-[(2,4-dioxo-1H-pyrimidine-6-carbonyl)amino]-2,2-dimethyl-1,3-dioxan-5-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 1400872-59-4
• 化学式: C₂₆H₃₅N₃O₁₅
• 分子量: 629.575
• InChiKey: ANKWNDHWEBOTJE-XSEKTIEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  229
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-(N-benzyloxycarbonyl)-2,2-dimethyl-1,3-dioxane 在 10% Pd/C 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 5-[O-(2l,3l,4l,6l-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-[N-(uracil-6-carboximido)]-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis and Preliminary Screening ofO-β-D-Galactopyranosides as Potential Mimic of UDP-GalpagainstMycobacterium tuberculosis

  摘要：

  O-Galactopyranosides were synthesized as potential mimics of uridine 5c-diphosphate galactopyranose (UDP-Galp), which is the substrate of the mutase enzyme involved in the mycobacterial cell wall biosynthesis by converting UDP-Galp to UDP-Galf. In vitro assay against the Mycobacterium tuberculosis H37Rv strain gave promising results with minimum inhibitory concentration (MIC) values in the range of 3.13 to 25 mu g/mL.

  DOI：

  10.1080/07328303.2011.654017