2,3-O-cyclohexylidene-β-D-ribofuranose | 177414-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-cyclohexylidene-β-D-ribofuranose
• 英文别名: (3A'R,4'R,6'R,6a'R)-6'-(hydroxymethyl)tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4'-ol；(3aR,4R,6R,6aR)-6-(hydroxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol
• CAS: 177414-91-4
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: AZDAIDRGKDVDCA-ZYUZMQFOSA-N

物化性质

• 沸点：
  423.3±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-cyclohexylidene-β-D-ribofuranose 、 1-(4-azidobut-2-yn-1-yl)thymine 以67%的产率得到1-((5-((((3a'R,4'R,6'R,6a'R)-4'-hydroxytetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-6'-yl)methoxy)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction

  摘要：

  Nucleoside analogs with the 4,5-dimethyl-NH-1,2,3-triazolo-linker between thymine and a carbohydrate, or a hydroxyalkoxyl, or phosphonomethoxyl residue, were obtained by the Bannert cascade reaction from 1-(4-azidobut-2-yn-1-yl)thymine and the carbohydrate or acyclic alcohol. The reaction conditions were developed on the basis of a thermal analysis of the starting azide and by the optimization of the reaction components ratio. The best results were obtained when the reaction cascade employed the azide/nucleophile molar ratio of 1114, at 55 degrees C, with no solvent addition. The reaction showed good discrimination between the pentofuranose hydroxyls, yielding triazoles linked at the carbohydrate 5'-oxygen atom. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.042

文献信息

• Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction
  作者：Mariola Koszytkowska-Stawińska、Wojciech Sas

  DOI：10.1016/j.tet.2013.01.042

  日期：2013.3

  Nucleoside analogs with the 4,5-dimethyl-NH-1,2,3-triazolo-linker between thymine and a carbohydrate, or a hydroxyalkoxyl, or phosphonomethoxyl residue, were obtained by the Bannert cascade reaction from 1-(4-azidobut-2-yn-1-yl)thymine and the carbohydrate or acyclic alcohol. The reaction conditions were developed on the basis of a thermal analysis of the starting azide and by the optimization of the reaction components ratio. The best results were obtained when the reaction cascade employed the azide/nucleophile molar ratio of 1114, at 55 degrees C, with no solvent addition. The reaction showed good discrimination between the pentofuranose hydroxyls, yielding triazoles linked at the carbohydrate 5'-oxygen atom. (C) 2013 Elsevier Ltd. All rights reserved.