1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil | 176895-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil
• CAS: 176895-45-7
• 化学式: C₁₇H₁₇N₃O₈
• 分子量: 391.337
• InChiKey: IEKKQODSYYHDTL-ONGIZVEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  145.92
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil 在 甲基磺酰氯 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 0.42h， 生成 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil
  参考文献：
  名称：

  Stereoselective Reactions OF 1-(4,6-O-Benzylidene-2,3-Didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil with some Nucleophiles¶

  摘要：

  Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (4b) gave the corresponding 2-(substituted-amino)-3-deoxy-3-nitro-beta-D-glucopyranosides (6a-f and 6h). Reaction of 4b with N,N'-carbonyldiimidazole directly gave 6g. Compound 4b was converted into the 2-deoxy analogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino analogue (10).

  DOI：

  10.1080/07328319608002131
• 作为产物：
  描述：

  苯甲醛 、 在 zinc(II) chloride 作用下， 反应 24.0h， 以15%的产率得到1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-galactopyranosyl)uracil
  参考文献：
  名称：

  Stereoselective Reactions OF 1-(4,6-O-Benzylidene-2,3-Didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil with some Nucleophiles¶

  摘要：

  Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (4b) gave the corresponding 2-(substituted-amino)-3-deoxy-3-nitro-beta-D-glucopyranosides (6a-f and 6h). Reaction of 4b with N,N'-carbonyldiimidazole directly gave 6g. Compound 4b was converted into the 2-deoxy analogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino analogue (10).

  DOI：

  10.1080/07328319608002131