5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-amino-2,2-dimethyl-1,3-dioxane | 1400872-56-1

• 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-amino-2,2-dimethyl-1,3-dioxane
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methoxy]oxan-2-yl]methyl acetate
• CAS: 1400872-56-1
• 化学式: C₂₁H₃₃NO₁₂
• 分子量: 491.493
• InChiKey: IYOPTBOZDPUZJW-ICBNADEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  13

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-amino-2,2-dimethyl-1,3-dioxane 、 异氰酸间氰基苯酯 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-[N-(3-cyanophenylurea)]-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：

  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 、 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-amino-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