1-(5-Amino-2,5-dideoxy-β-D-erythro-pentofuranosyl)thieno<2,3-d>pyrimidine-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 1-(5-Amino-2,5-dideoxy-β-D-erythro-pentofuranosyl)thieno<2,3-d>pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-(5-Amino-2,5-dideoxy-beta-d-erythro-pentofuranosyl)thieno[2,3-d]pyrimidine-2,4(1h,3h)-dione；1-[(2R,4S,5R)-5-(aminomethyl)-4-hydroxyoxolan-2-yl]thieno[2,3-d]pyrimidine-2,4-dione
• 化学式: C₁₁H₁₃N₃O₄S
• 分子量: 283.308
• InChiKey: DTLCJEHCQLUZKL-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(5-Azido-2,5-dideoxy-β-D-erythro-pentofuranosyl)thieno<2,3-d>pyrimidine-2,4(1H,3H)-dione 在 吡啶 、 ammonium hydroxide 、 三苯基膦 作用下， 生成 1-(5-Amino-2,5-dideoxy-β-D-erythro-pentofuranosyl)thieno<2,3-d>pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 5?-amino- and 5?-azido-2?,5?-dideoxy nucleosides from thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

  摘要：

  Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (4) was silylated and condensed with methyl 5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (2) in the presence of TMS triflate to afford the corresponding protected nucleoside 6 and acyclic nucleoside 7. Deprotection of 6 with MeONa/MeOH at room temperature gave 1-(5-azido-2,5-dideoxy-alpha-D-erythro-pentofuranosyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (8) and the corresponding beta anomer 9, whereas compound 7 yielded 5-azido-2,5-dideoxy-1-(2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d]pyrimidin-1-yl)-1-O-methyl-D-erythro-pentitol (10) under the same reaction conditions. 1-(5-Amino-2,5-dideoxy-beta-D-erythro-pentofuranosyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (11) was obtained on treating 9 with Ph(3)P in pyridine followed by hyrolysis with NH4OH. The anomeric nucleosides 14 and 15 and the corresponding acyclic nucleoside 16 were obtained when 4 was trimethylsilylated and condensed with methyl 2-deoxy-3,5-di-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (3) followed by deprotection with MeONa in MeOH. Compounds 8 and 9 were also obtained when the anomeric mixture 14/15 was treated with a mixture of NaN3, Ph(3)P, and CBr4 in dry DMF at room temperature.

  DOI：

  10.1007/bf00807434

文献信息

• Synthesis of 5?-amino- and 5?-azido-2?,5?-dideoxy nucleosides from thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
  作者：A. A. El-Barbary、N. R. El-Brollosy、E. B. Pedersen、C. Nielsen

  DOI：10.1007/bf00807434

  日期：1995.5

  Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (4) was silylated and condensed with methyl 5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (2) in the presence of TMS triflate to afford the corresponding protected nucleoside 6 and acyclic nucleoside 7. Deprotection of 6 with MeONa/MeOH at room temperature gave 1-(5-azido-2,5-dideoxy-alpha-D-erythro-pentofuranosyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (8) and the corresponding beta anomer 9, whereas compound 7 yielded 5-azido-2,5-dideoxy-1-(2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d]pyrimidin-1-yl)-1-O-methyl-D-erythro-pentitol (10) under the same reaction conditions. 1-(5-Amino-2,5-dideoxy-beta-D-erythro-pentofuranosyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (11) was obtained on treating 9 with Ph(3)P in pyridine followed by hyrolysis with NH4OH. The anomeric nucleosides 14 and 15 and the corresponding acyclic nucleoside 16 were obtained when 4 was trimethylsilylated and condensed with methyl 2-deoxy-3,5-di-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (3) followed by deprotection with MeONa in MeOH. Compounds 8 and 9 were also obtained when the anomeric mixture 14/15 was treated with a mixture of NaN3, Ph(3)P, and CBr4 in dry DMF at room temperature.