(2S,3R)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester | 152982-19-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (2S,3R)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester
• 英文别名: ethyl (2S,3R)-3-hydroxy-2-methyl-3-phenyl-2-phenylmethoxypropanoate
• CAS: 152982-19-9
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: OYPPYQFTDGJUNH-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯甲醛 、 ((E)-2-Benzyloxy-1-ethoxy-propenyloxy)-trimethyl-silane 在 tin(II) trifluoromethanesulfonate 、 (S)-1-methyl-2-<(N-naphthylamino)methyl>pyrrolidine 、 二乙酸二丁基锡 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester 、 (2R,3S)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester 、 (2R,3R)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of the a-Hydroxy-a-methyl-b-hydroxy Units via Asymmetric Aldol Reaction

  摘要：

  The alpha-hydroxy-alpha-methyl-beta-hydroxy units are enantioselectively prepared by way of asymmetric aldol reactions between both achiral beta,beta-disubstituted silyl enolates and aldehydes. (-)-2-C-Methyl-D-threono-1,4-lactone is conveniently synthesized by using this reaction.

  DOI：

  10.3987/com-93-s(t)138

文献信息

• An Efficient Method for the Preparation of Chiral Synthons Starting from Racemic Compounds by Way of Asymmetric Synthesis
  作者：Shu Kobayashi、Isamu Shiina、Jun Izumi、Teruaki Mukaiyama

  DOI：10.1246/cl.1992.373

  日期：1992.3

  Optically active α-alkoxy-α-methyl-β-hydroxy ester derivatives are prepared starting from racemic α-alkoxy propionic acid ester derivatives by way of asymmetric aldol reaction of the corresponding achiral intermediates. (−)-2-C-Methyl-D-threono-1,4-lactone is conveniently synthesized by using this methodology.

  旋光α-烷氧基-α-甲基-β-羟基酯衍生物由外消旋α-烷氧基丙酸酯衍生物通过相应非手性中间体的不对称羟醛反应制备。(-)-2-C-Methyl-D-threono-1,4-lactone 可以使用这种方法方便地合成。