Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(1H-tetrazol-5-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester | 128364-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(1H-tetrazol-5-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
• 英文别名: 5-(5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-tetrazole
• CAS: 128364-98-7
• 化学式: C₁₆H₁₈N₄O₅
• 分子量: 346.343
• InChiKey: NNMWVMFDWFXKSA-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.45
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(1H-tetrazol-5-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 5-<3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-1H-tetrazole
  参考文献：
  名称：

  Preparation and Utility of 5-β-D-Ribofuranosyl-1H-tetrazole as a Key Synthon for C-Nucleoside Synthesis

  摘要：

  A synthesis of 5-beta-D-ribofuranosyl-1H-tetrazole (2) and 5-beta-D-ribo-furanosyl-1,3,4-oxadiazole-2(3H)-one (9) derivatives is described. Ring transformations of 2 have been investigated in an effort to establish the stability of this synthon for further use in dipolar cycloaddition reactions.

  DOI：

  10.1080/15257779408013218
• 作为产物：
  描述：

  5-O-benzoyl-2,3-di-O-isopropylidene-β-D-ribofuranosyl-1-carbonitrile 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以67%的产率得到Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(1H-tetrazol-5-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  Preparation and Utility of 5-β-D-Ribofuranosyl-1H-tetrazole as a Key Synthon for C-Nucleoside Synthesis

  摘要：

  A synthesis of 5-beta-D-ribofuranosyl-1H-tetrazole (2) and 5-beta-D-ribo-furanosyl-1,3,4-oxadiazole-2(3H)-one (9) derivatives is described. Ring transformations of 2 have been investigated in an effort to establish the stability of this synthon for further use in dipolar cycloaddition reactions.

  DOI：

  10.1080/15257779408013218

文献信息

• Novel regioselective N-alkylations of 5-substituted-2H-tetrazoles
  作者：Marija Prhavc、Jozˇe Kobe

  DOI：10.1016/s0040-4039(00)98819-1

  日期：1990.1

  Regioselective alkylation of 5-substituted-2H-tetrazoles1 to 2-alkyl derivatives 3 was achievedvia decar☐ylative alkylation with alkyl cyanoformates. Lesser selectivity was observed with chloroformates.

  通过用烷基氰甲酸酯的十烷基化烷基化，实现了5-取代的2H-四唑1至2-烷基衍生物3的区域选择性烷基化。用氯甲酸酯观察到较小的选择性。