5(R)-benzyloxy-4(R)-benzyloxymethyl-tetrahydropyrimidin-2-one | 155650-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5(R)-benzyloxy-4(R)-benzyloxymethyl-tetrahydropyrimidin-2-one
• CAS: 155650-45-6
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: MCSGQJKBLNCIJJ-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59.59
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5(R)-benzyloxy-4(R)-benzyloxymethyl-tetrahydropyrimidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以85%的产率得到5(R)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one
  参考文献：
  名称：

  Competitive inhibition of glycoside hydrolases by 1,3-diamino-1,3-dideoxy-tetritols and their cyclic carbonic and thiocarbonic amides

  摘要：

  1,3-Diamino-1,3-dideoxy-D-threitol (1) and the corresponding 1,3-diamino-1,3-dideoxy-D-erythritol (2) were synthesised starting from D-glucose and L-arabinose, respectively. These acyclic diamines inhibited competitively both beta-D-glucosidase from sweet almond emulsin and beta-D-galactosidase from E. coli with K-1-values ranging from 3 to 10 mM. When the suitably blocked diamines were reacted with activated carbonic and thiocarbonic acid derivatives, cyclic urea 5(R)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one (13), 5(S)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one (15) and thiourea 5(S)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-thione (18) derivatives were obtained, which conformationally resemble the envelope structure of the D-glucopyranosyl or the D-galactopyranosyl cation. The cyclic carbonamides showed extremely weak competitive inhibition but only with their corresponding enzymes. Compounds 15 and 18 exist, as indicated by H-1 NMR spectroscopy, in an unexpected E-conformation with axial substituents. Upon per-O-acetylation the expected conformation with equatorial substituents is adopted.

  DOI：

  10.1016/0008-6215(93)84152-v
• 作为产物：
  描述：

  1,3-di-O-benzyl-2,4-O-benzylidene-D-erythritol 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 77.0h， 生成 5(R)-benzyloxy-4(R)-benzyloxymethyl-tetrahydropyrimidin-2-one
  参考文献：
  名称：

  Competitive inhibition of glycoside hydrolases by 1,3-diamino-1,3-dideoxy-tetritols and their cyclic carbonic and thiocarbonic amides

  摘要：

  1,3-Diamino-1,3-dideoxy-D-threitol (1) and the corresponding 1,3-diamino-1,3-dideoxy-D-erythritol (2) were synthesised starting from D-glucose and L-arabinose, respectively. These acyclic diamines inhibited competitively both beta-D-glucosidase from sweet almond emulsin and beta-D-galactosidase from E. coli with K-1-values ranging from 3 to 10 mM. When the suitably blocked diamines were reacted with activated carbonic and thiocarbonic acid derivatives, cyclic urea 5(R)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one (13), 5(S)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one (15) and thiourea 5(S)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-thione (18) derivatives were obtained, which conformationally resemble the envelope structure of the D-glucopyranosyl or the D-galactopyranosyl cation. The cyclic carbonamides showed extremely weak competitive inhibition but only with their corresponding enzymes. Compounds 15 and 18 exist, as indicated by H-1 NMR spectroscopy, in an unexpected E-conformation with axial substituents. Upon per-O-acetylation the expected conformation with equatorial substituents is adopted.

  DOI：

  10.1016/0008-6215(93)84152-v