1-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-ribo-hex-3-ulopyranosyl)-6-azauracil | 170872-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-ribo-hex-3-ulopyranosyl)-6-azauracil
• 英文别名: N-[(4aR,6R,7S,8aR)-6-(3,5-dioxo-1,2,4-triazin-2-yl)-2,2-dimethyl-8-oxo-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 170872-07-8
• 化学式: C₁₄H₁₈N₄O₇
• 分子量: 354.32
• InChiKey: MCTLJFYFZAMEFB-COYOAVQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-ribo-hex-3-ulopyranosyl)-6-azauracil 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 17.5h， 生成 1-(2-acetamido-2-deoxy-β-D-allopyranosyl)-6-azauracil
  参考文献：
  名称：

  Synthesis and Reactions of Some Glycosylamine Derivatives of 6-Azauracil Nucleosides

  摘要：

  Reaction of the silylated 6-azauracil (2) with 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucose (3) gave 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-6-azauracil (4), which gave the free nucleoside 5 on deblocking. Acetalation of 5 gave the monoacetal 6 which was oxidized into the ketone 7. Reduction of 7 gave the allo-nucleoside 9 which on hydrolysis afforded the free nucleoside 10. Alternatively, compound 10 was obtained from mesylation of 6 to give 8 followed by subsequent acetolysis and hydrolysis.

  DOI：

  10.1080/15257779508010695
• 作为产物：
  描述：

  1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-azauracil 在 sodium methylate 、 phosphorus pentoxide 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-ribo-hex-3-ulopyranosyl)-6-azauracil
  参考文献：
  名称：

  Synthesis and Reactions of Some Glycosylamine Derivatives of 6-Azauracil Nucleosides

  摘要：

  Reaction of the silylated 6-azauracil (2) with 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucose (3) gave 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-6-azauracil (4), which gave the free nucleoside 5 on deblocking. Acetalation of 5 gave the monoacetal 6 which was oxidized into the ketone 7. Reduction of 7 gave the allo-nucleoside 9 which on hydrolysis afforded the free nucleoside 10. Alternatively, compound 10 was obtained from mesylation of 6 to give 8 followed by subsequent acetolysis and hydrolysis.

  DOI：

  10.1080/15257779508010695