methyl (R,R)-2,3-dihydroxy-2,3-O-isopropylidenepent-4-enoate | 183889-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (R,R)-2,3-dihydroxy-2,3-O-isopropylidenepent-4-enoate
• 英文别名: methyl (4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 183889-09-0
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: VLYSFROIIVAENJ-BQBZGAKWSA-N

物化性质

• 沸点：
  214.7±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R,R)-2,3-dihydroxy-2,3-O-isopropylidenepent-4-enoate 在 四氧化锇 N-甲基吲哚酮 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 0.1h， 以55%的产率得到2,3-O-Isopropylidene-L-ribono-1,4-lactone
  参考文献：
  名称：

  Stereoselective Transformations Leading to Pentono-1,4-Lactones1

  摘要：

  The readily available 2,3-O-isopropylidene-D-erythrose has been stereoselectively transformed into L-ribono and D/L lyxonolactone derivatives via dihydroxylation, iodolactonisation and epoxidation. Also D-ribono-1,4-lactone was converted into L-lyxono-1,4-lactone. These lactones are considered as important starting materials for the synthesis of several chiral compounds. Our observations during these transformations are also presented.

  DOI：

  10.1080/07328309608005703
• 作为产物：
  描述：

  (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 在 1‐methyl‐2‐azaadamantane‐N‐oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 aq. phosphate buffer 、 乙醚 、 乙腈 为溶剂， 反应 1.0h， 生成 methyl (R,R)-2,3-dihydroxy-2,3-O-isopropylidenepent-4-enoate
  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