苯甲腈,4-(2-氨基-4-嘧啶基)- | 98050-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯甲腈,4-(2-氨基-4-嘧啶基)-
• 英文名称: methyl α-D-threo-pentodialdo-1,4-furanoside
• 英文别名: (2S,3R,5S)-3-hydroxy-5-methoxyoxolane-2-carbaldehyde
• CAS: 98050-06-7
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: LQOPPFCHYHRXSN-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲腈,4-(2-氨基-4-嘧啶基)- 生成 (2R)-2-hydroxy-2-[(2S,3R,5S)-3-hydroxy-5-methoxyoxolan-2-yl]acetonitrile
  参考文献：
  名称：

  WALKER, THOMAS E.;EHLER, DEBORAH S.;UNKEFER, CLIFFORD J., CARBOHYDR. RES., 181,(1988) C. 125-134

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R)-1-[(3R,5S)-3-hydroxy-5-methoxyoxolan-2-yl]ethane-1,2-diol 生成 苯甲腈,4-(2-氨基-4-嘧啶基)-
  参考文献：
  名称：

  WALKER, THOMAS E.;EHLER, DEBORAH S.;UNKEFER, CLIFFORD J., CARBOHYDR. RES., 181,(1988) C. 125-134

  摘要：

  DOI：

文献信息

• Synthesis of 2-deoxy-d-arabino-(6-13C)hexose
  作者：Thomas E. Walker、Deborah S. Ehler、Clifford J. Unkefer

  DOI：10.1016/0008-6215(88)84028-x

  日期：1988.10

  2-Deoxy-D-arabino-[6-13C]hexose (10), to be used to test the stability of 2-deoxy-D-arabino-hexose 6-phosphate in brain tissue, was prepared. 2-Deoxy-D-arabino-hexose was labeled at C-6 because of the large difference in chemical shift between C-6 in the free sugar and C-6 in the 6-phosphate. The synthetic scheme resembled that used for the synthesis of D-[6-13C]glucose that involved the removal of C-6 from D-glucose followed by its replacement with 13C. The protected derivative methyl 2-deoxy-alpha-D-arabino-hexofuranoside was prepared, using trifluoroacetic acid in methanol. This was treated with periodate, which cleaves only between C-5 and C-6, to afford an aldehyde which reacted directly with K13CN to give a mixture of the D-arabino and L-xylo nitriles. The enriched nitriles were reduced with hydrogen in the presence of 5% Pd-carbon catalyst to a mixture of 6-aldehydo sugars. These were reduced with NaBH4 to a mixture of the two labeled methyl furanosides. Acid hydrolysis followed by ion-exchange chromatography on AG-50(Ca2+) resin at 65 degrees gave 10 in an overall yield of 16% from K13CN.