(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-6-(2-hydroxyethyl)-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-2-ylmethyl ester | 890028-14-5

• 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: (+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-6-(2-hydroxyethyl)-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-2-ylmethyl ester
• CAS: 890028-14-5
• 化学式: C₂₃H₃₂N₂O₁₀
• 分子量: 496.514
• InChiKey: CPXVUWVDWLIXCA-FRPRTOITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  160.5
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-6-(2-hydroxyethyl)-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-2-ylmethyl ester 在 盐酸 、 戴斯-马丁氧化剂 、 silver carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 (-)-3,5-dinitrobenzoic acid (4aS,5S,7aS,3'S,5'R)-7a-methylhexahydrocyclopenta[c]pyran-3(1H)-one-5-spiro-2'-(3'-methyltetrahydrofuran)-5'-ylmethyl ester
  参考文献：
  名称：

  Synthetic Studies on (+)-Ophiobolin A:  Asymmetric Synthesis of the Spirocyclic CD-Ring Moiety

  摘要：

  Asymmetric synthesis of the spirocyclic CID-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety la in the presence of a Lewis acid.

  DOI：

  10.1021/ol060437x
• 作为产物：
  描述：

  (3S,5R)-5-Iodomethyl-3-methyldihydrofuran-2(3H)-one 在 咪唑 、 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 Ti(OiPr)Cl3 、 四丁基氟化铵 、 叔丁基锂 、 sodium 2,2,2-trifluoroacetate 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 4.25h， 生成 (+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-6-(2-hydroxyethyl)-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-2-ylmethyl ester
  参考文献：
  名称：

  Synthetic Studies on (+)-Ophiobolin A:  Asymmetric Synthesis of the Spirocyclic CD-Ring Moiety

  摘要：

  Asymmetric synthesis of the spirocyclic CID-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety la in the presence of a Lewis acid.

  DOI：

  10.1021/ol060437x