dimethyl (3aR,4R,6aS)-4-dodecyl-2,2-dimethyl-6-oxo-6aH-furo[3,4-d][1,3]dioxole-3a,4-dicarboxylate | 1426147-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl (3aR,4R,6aS)-4-dodecyl-2,2-dimethyl-6-oxo-6aH-furo[3,4-d][1,3]dioxole-3a,4-dicarboxylate
• CAS: 1426147-59-2
• 化学式: C₂₃H₃₈O₈
• 分子量: 442.55
• InChiKey: DCRODJNHISJAJS-VSDWSMLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl (3aR,4R,6aS)-4-dodecyl-2,2-dimethyl-6-oxo-6aH-furo[3,4-d][1,3]dioxole-3a,4-dicarboxylate 在 碘 作用下， 以 甲醇 为溶剂， 反应 45.0h， 以84%的产率得到dimethyl (2R,3R,4S)-2-dodecyl-3,4-dihydroxy-5-oxooxolane-2,3-dicarboxylate
  参考文献：
  名称：

  Application of a Stereoselective Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3]-Sigmatropic Rearrangement of an α-Diazo-β-keto Ester to the Synthesis of 2-epi-Cinatrin C1 Dimethyl Ester

  摘要：

  The Rh-2(OAc)(4)-catalyzed oxonium ylide formation-[2,3]-sigmatropic rearrangement of a highly functionalized alpha-diazo-beta-keto ester derived from D-glucose proceeded stereoselectively to give the corresponding tetrahydrofuran-3-one as a single diastereomer in high yield. This reaction was applied to the synthesis of 2-epi-cinatrin C-1 dimethyl ester as a key step.

  DOI：

  10.1055/s-0032-1317694
• 作为产物：
  描述：

  dimethyl (3aR,4R,6R,6aR)-4-dodecyl-6-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxole-3a,4-dicarboxylate 在 重铬酸吡啶 、 乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以71%的产率得到dimethyl (3aR,4R,6aS)-4-dodecyl-2,2-dimethyl-6-oxo-6aH-furo[3,4-d][1,3]dioxole-3a,4-dicarboxylate
  参考文献：
  名称：

  Application of a Stereoselective Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3]-Sigmatropic Rearrangement of an α-Diazo-β-keto Ester to the Synthesis of 2-epi-Cinatrin C1 Dimethyl Ester

  摘要：

  The Rh-2(OAc)(4)-catalyzed oxonium ylide formation-[2,3]-sigmatropic rearrangement of a highly functionalized alpha-diazo-beta-keto ester derived from D-glucose proceeded stereoselectively to give the corresponding tetrahydrofuran-3-one as a single diastereomer in high yield. This reaction was applied to the synthesis of 2-epi-cinatrin C-1 dimethyl ester as a key step.

  DOI：

  10.1055/s-0032-1317694