1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6,7-diphenyllumazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6,7-diphenyllumazine
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-6,7-diphenylpteridine-2,4-dione
• 化学式: C₂₃H₁₉N₇O₄
• 分子量: 457.448
• InChiKey: BSPRSKCGZMBXDR-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,4(1H,3H)-蝶啶二酮,6,7-二苯基- 在 吡啶 、 4-二甲氨基吡啶 、 ammonium sulfate 、 sodium azide 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 sodium methylate 、 对甲苯磺酸 、 一水合肼 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6,7-diphenyllumazine
  参考文献：
  名称：

  Nucleosides. LIV¹Synthesis and Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides

  摘要：

  The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7-diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-beta-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (1 7, 3 4, 4 9) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 1 9, 2 9 and 4 7 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-beta-D- glycero-pentofuranosyl)-6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-beta-D-erythro-pentofuranosyl)- 6,7-diphenyllumazine and the corresponding 6,7-dimethyllumazine (2 6) via their 5'-O-p-toluoyl- (2 0, 3 0), and 3'-deoxy-3'-iodo derivatives (2 4, 3 1) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.

  DOI：

  10.1080/15257779408013278