tret-butyl (4S,5S)-5-((S)-2-ethoxy-1-hydroxy-2-oxoethyl)-4-hydroxy-2-methyl-4,5-dihydrofuran-3-carboxylate | 1259569-67-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: tret-butyl (4S,5S)-5-((S)-2-ethoxy-1-hydroxy-2-oxoethyl)-4-hydroxy-2-methyl-4,5-dihydrofuran-3-carboxylate
• 英文别名: tert-butyl (2S,3S)-2-[(1S)-2-ethoxy-1-hydroxy-2-oxoethyl]-3-hydroxy-5-methyl-2,3-dihydrofuran-4-carboxylate
• CAS: 1259569-67-9
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: LQQNFQOYBRNISC-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酰乙酸叔丁酯 、 乙基(2S,3S)-3-甲酰基-2-环氧乙烷羧酸酯 在 magnesium sulfate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tret-butyl (4R,5S)-5-((S)-2-ethoxy-1-hydroxy-2-oxoethyl)-4-hydroxy-2-methyl-4,5-dihydrofuran-3-carboxylate 、 tret-butyl (4S,5S)-5-((S)-2-ethoxy-1-hydroxy-2-oxoethyl)-4-hydroxy-2-methyl-4,5-dihydrofuran-3-carboxylate
  参考文献：
  名称：

  An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes

  摘要：

  The first enantioselective methodology for the synthesis of electron-poor 2-hydroxyalkyl- and 2-aminoalkyl furanes is demonstrated in this study. It utilizes a highly stereoselective organocatalytic one-pot reaction cascade: epoxidation or aziridination of alpha,beta-unsaturated aldehydes followed by Feist-Benary reaction of various 1,3-dicarbonyl compounds to give the target furanes. This efficient multibond forming reaction cascade benefits from low catalyst loadings and readily available starting materials. Furthermore, the possibility to interrupt the reaction sequence at the stage of the corresponding optically active 2-hydroxyalkyl- and 2-aminoalkyl 2,3-dihydrofuranes with three stereogenic centers is also presented. Finally, models which account for the formation of the optically active 2,3-dihydrofuranes are proposed.

  DOI：

  10.1021/ja108247t

文献信息

• An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes
  作者：Łukasz Albrecht、Lars Krogager Ransborg、Björn Gschwend、Karl Anker Jørgensen

  DOI：10.1021/ja108247t

  日期：2010.12.22

  The first enantioselective methodology for the synthesis of electron-poor 2-hydroxyalkyl- and 2-aminoalkyl furanes is demonstrated in this study. It utilizes a highly stereoselective organocatalytic one-pot reaction cascade: epoxidation or aziridination of alpha,beta-unsaturated aldehydes followed by Feist-Benary reaction of various 1,3-dicarbonyl compounds to give the target furanes. This efficient multibond forming reaction cascade benefits from low catalyst loadings and readily available starting materials. Furthermore, the possibility to interrupt the reaction sequence at the stage of the corresponding optically active 2-hydroxyalkyl- and 2-aminoalkyl 2,3-dihydrofuranes with three stereogenic centers is also presented. Finally, models which account for the formation of the optically active 2,3-dihydrofuranes are proposed.