1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine | 159228-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine
• CAS: 159228-09-8
• 化学式: C₂₅H₂₀N₄O₈
• 分子量: 504.456
• InChiKey: URGPPDDZXVUXRI-NSAZKJPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  162.7
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 2,2'-anhydro-1-(3,5-di-O-benzoyl-β-D-lyxofuranosyl)-lumazine
  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
• 作为产物：
  描述：

  1,2-di-O-acetyl-3,5-di-O-benzoyl-D-xylofuranose 在 吡啶 、 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 一水合肼 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 反应 8.0h， 生成 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine
  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