2-((3aR,4S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-oxoacetic acid | 1400695-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3aR,4S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-oxoacetic acid
• CAS: 1400695-54-6
• 化学式: C₁₆H₁₈O₇
• 分子量: 322.315
• InChiKey: ZOTOZUBXVZUECN-OSFYFWSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (benzyl 2,3-O-isopropylidene-α-D-mannofuranosid)uronic acid 在 Me-AZADO+Cl- 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到2-((3aR,4S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-oxoacetic acid
  参考文献：
  名称：

  Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids

  摘要：

  The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO2 caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.

  DOI：

  10.1021/ol3021429