methyl (3aS,4S,6R,6aS)-4-bromo-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate | 136449-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3aS,4S,6R,6aS)-4-bromo-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 136449-52-0
• 化学式: C₁₄H₂₁BrO₇
• 分子量: 381.221
• InChiKey: MUWBIFFNBVKLNN-DJRVLGHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (3aS,4S,6R,6aS)-4-bromo-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到Methyl 2,5-anhydro-2-azido-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptonate
  参考文献：
  名称：

  Approach to oxetane and furan nucleosides with an anomeric carbon substituent: Nucleophilic substitution at highly hindered α-bromo-oxetane- and -tetrahydrofuran-carboxylates

  摘要：

  Treatment of oxetane-2-carboxylic esters with lithium hexamethyldisilazide generates anions which can be trapped with carbon tetrabromide to give epimeric 2-bromo-oxetane-2-carboxylic esters which undergo rapid displacement of bromide by azide with clean inversion of configuration. This may provide an approach to the synthesis of oxetane nucleosides possessing a carbon substituent at the anomeric position. An example of similar chemistry applied to tetrahydrofuran-2-carboxylic ester is also reported.

  DOI：

  10.1016/0040-4039(91)80836-u
• 作为产物：
  描述：

  methyl (3aS,4R,6R,6aS)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate 在 四溴化碳 、 lithium hexamethyldisilazane 作用下， 生成 methyl (3aS,4S,6R,6aS)-4-bromo-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate 、
  参考文献：
  名称：

  Approach to oxetane and furan nucleosides with an anomeric carbon substituent: Nucleophilic substitution at highly hindered α-bromo-oxetane- and -tetrahydrofuran-carboxylates

  摘要：

  Treatment of oxetane-2-carboxylic esters with lithium hexamethyldisilazide generates anions which can be trapped with carbon tetrabromide to give epimeric 2-bromo-oxetane-2-carboxylic esters which undergo rapid displacement of bromide by azide with clean inversion of configuration. This may provide an approach to the synthesis of oxetane nucleosides possessing a carbon substituent at the anomeric position. An example of similar chemistry applied to tetrahydrofuran-2-carboxylic ester is also reported.

  DOI：

  10.1016/0040-4039(91)80836-u