5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-(N-benzyloxycarbonyl)-2,2-dimethyl-1,3-dioxane | 1400872-55-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-(N-benzyloxycarbonyl)-2,2-dimethyl-1,3-dioxane
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[2,2-dimethyl-5-(phenylmethoxycarbonylamino)-1,3-dioxan-5-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 1400872-55-0
• 化学式: C₂₉H₃₉NO₁₄
• 分子量: 625.627
• InChiKey: AYOJNCFPSRHEFH-RSFKBIFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  180
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  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-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-[N-{(S)-3-(1-(tert-butoxycarbonyl)-1H-imidazol-4-yl)-2-(tert-butoxycarbonylamino)propanamido}]-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
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide 、 (5-benzyloxycarbonylamino-2,2-dimethyl-1,3-dioxan-5-yl)methanol 在 mercury(II) cyanide 作用下， 以 乙腈 为溶剂， 以75%的产率得到5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-(N-benzyloxycarbonyl)-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