[2S*,3S*]-4-formyl-3-hydroxy-2,3-dihydro-furan-2,3-dicarboxylic acid diethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2S*,3S*]-4-formyl-3-hydroxy-2,3-dihydro-furan-2,3-dicarboxylic acid diethyl ester
• 英文别名: diethyl (2S,3S)-4-formyl-3-hydroxy-2H-furan-2,3-dicarboxylate
• 化学式: C₁₁H₁₄O₇
• 分子量: 258.228
• InChiKey: LAEDBJJBABYSLI-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙二醛 、 bromo-oxo-succinic acid diethyl ester 在 盐酸 、 三乙胺 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 15.0h， 以30%的产率得到[2S*,3S*]-4-formyl-3-hydroxy-2,3-dihydro-furan-2,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Scope and Diastereoselectivity of the “Interrupted” Feist−Bénary Reaction

  摘要：

  [GRAPHICS]The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Benary reaction, conveniently produces highly substituted dihydrofurans. We show here that this reaction is quite general with respect to the nature of the beta-dicarbonyl compound, proceeding with beta-ketoesters, beta-oxopropionates, beta-diketones, and beta-dialdehydes. We also show that the diastereoselectivity of this reaction depends on the acidity of the nucleophile.

  DOI：

  10.1021/ol0169978

文献信息

• Rapid Synthesis of the 7-Deoxy Zaragozic Acid Core
  作者：Michael A. Calter、Cheng Zhu、Rene J. Lachicotte

  DOI：10.1021/ol0169980

  日期：2002.1.1

  text] We have developed an efficient synthesis of the 7-deoxy zaragozic acid core. The synthesis begins with a Feist-Bénary reaction that assembles all three carbons of the polycarboxylic acid portion of the core. This reaction is followed by highly diastereoselective aldol and dihydroxylation reactions that set the remaining stereocenters of the core. The synthesis finishes with lactol oxidation and

  [反应：见正文]我们已经开发出7-脱氧zaragozic核心的有效合成方法。合成从Feist-Bénary反应开始，该反应将核心的多元羧酸部分的所有三个碳组装在一起。该反应之后是高度非对映选择性的羟醛和二羟基化反应，其设定了核的其余立体中心。合成过程以乳糖醇氧化和内酯醇解/缩酮形成反应完成，以构建核心的双环系统。
• Scope and Diastereoselectivity of the “Interrupted” Feist−Bénary Reaction
  作者：Michael A. Calter、Cheng Zhu

  DOI：10.1021/ol0169978

  日期：2002.1.1

  [GRAPHICS]The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Benary reaction, conveniently produces highly substituted dihydrofurans. We show here that this reaction is quite general with respect to the nature of the beta-dicarbonyl compound, proceeding with beta-ketoesters, beta-oxopropionates, beta-diketones, and beta-dialdehydes. We also show that the diastereoselectivity of this reaction depends on the acidity of the nucleophile.