1-(2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-glucopyranosyl)-N4-benzoylcytosine | 1389345-08-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-glucopyranosyl)-N4-benzoylcytosine
• CAS: 1389345-08-7
• 化学式: C₂₃H₂₄N₆O₉
• 分子量: 528.478
• InChiKey: ZFDSILXQTAAXBB-NEHCWNBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  200.88
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-glucopyranosyl)-N4-benzoylcytosine 在 氨 作用下， 以 甲醇 为溶剂， 以71%的产率得到1-(3-azido-3-deoxy-β-D-glucopyranosyl)-cytosine
  参考文献：
  名称：

  Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides

  摘要：

  This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-alpha-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3'-amino-3'-deoxy-beta-D-glucopyranonucleosides. The desired 1-(3'-amino-3'-deoxy-beta-D-allopyranosyl) 5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.

  DOI：

  10.1080/15257770.2012.696759
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose 在 sodium azide 、 六甲基二硅氮烷 、 糖精 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.5h， 生成 1-(2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-glucopyranosyl)-N4-benzoylcytosine
  参考文献：
  名称：

  Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides

  摘要：

  This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-alpha-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3'-amino-3'-deoxy-beta-D-glucopyranonucleosides. The desired 1-(3'-amino-3'-deoxy-beta-D-allopyranosyl) 5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.

  DOI：

  10.1080/15257770.2012.696759