4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-cyanocrotononitrile | 405510-22-7

• 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: 4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-cyanocrotononitrile
• 英文别名: [(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-(3,3-dicyanoprop-2-enyl)oxan-2-yl]methyl acetate
• CAS: 405510-22-7
• 化学式: C₁₉H₂₂N₂O₉
• 分子量: 422.392
• InChiKey: ITEPOVHBJFDELX-UJWQCDCRSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  526.3±45.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-cyanocrotononitrile 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以55.4%的产率得到2-amino-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)thiophene-3-carbonitrile
  参考文献：
  名称：

  SYNTHESIS OF (2,3,4,6-TETRA-O-ACETYL-α-D-GLYCOPYRANOSYL) THIOPHENE DERIVATIVES AS NEW C-NUCLEOSIDE ANALOGUES1

  摘要：

  Treatment of 2-(2,3,4,6-tetra-O-acetyl-alpha -D-glucopyranosyl)ethanal (1a) and 2(2,3,4,6-tetra-O-acetyl- alpha -D-galactopyranosyl)ethanal (lb), respectively, with malononitrile in the presence of silica gel provided the corresponding 4[2,3,4,6-tetra-O-acetyl-alpha -D-glycopyranosyl]-2-cyanocrotononitriles (2a) and (2b). Starting from 2a and 2b, respectively, cyclizations with sulfur and triethylamine yielded 5-[2,3,4,6-tetra-O-acetyl-alpha -D-glycopyranosyl]-2-aminothiophene-3-carbonitriles (3a) and (3b). Further cyclizations could be achieved by utilizing of triethyl orthoformate/ammonia to furnish the 6-(alpha -D-glycopyranosyl)thieno[2,3-dlpyriniidine-4-amines 4a and 4b.

  DOI：

  10.1081/car-100108282
• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal 、 丙二腈 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-cyanocrotononitrile
  参考文献：
  名称：

  SYNTHESIS OF (2,3,4,6-TETRA-O-ACETYL-α-D-GLYCOPYRANOSYL) THIOPHENE DERIVATIVES AS NEW C-NUCLEOSIDE ANALOGUES1

  摘要：

  Treatment of 2-(2,3,4,6-tetra-O-acetyl-alpha -D-glucopyranosyl)ethanal (1a) and 2(2,3,4,6-tetra-O-acetyl- alpha -D-galactopyranosyl)ethanal (lb), respectively, with malononitrile in the presence of silica gel provided the corresponding 4[2,3,4,6-tetra-O-acetyl-alpha -D-glycopyranosyl]-2-cyanocrotononitriles (2a) and (2b). Starting from 2a and 2b, respectively, cyclizations with sulfur and triethylamine yielded 5-[2,3,4,6-tetra-O-acetyl-alpha -D-glycopyranosyl]-2-aminothiophene-3-carbonitriles (3a) and (3b). Further cyclizations could be achieved by utilizing of triethyl orthoformate/ammonia to furnish the 6-(alpha -D-glycopyranosyl)thieno[2,3-dlpyriniidine-4-amines 4a and 4b.

  DOI：

  10.1081/car-100108282