(2R,3R)-3-Hydroxy-2-((R)-hydroxy-phenyl-methyl)-butyric acid methyl ester | 132016-64-9

• 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: (2R,3R)-3-Hydroxy-2-((R)-hydroxy-phenyl-methyl)-butyric acid methyl ester
• 英文别名: methyl (2R,3R)-3-hydroxy-2-[(R)-hydroxy(phenyl)methyl]butanoate
• CAS: 132016-64-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: JIIGTRBYXHJALA-IEBDPFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛 、 (Z)-(R)-1,3-bis(triethylsilyloxy)-1-methoxy-1-butene 在 Eu(fod)3 盐酸 作用下， 生成 (2R,3R)-3-Hydroxy-2-((R)-hydroxy-phenyl-methyl)-butyric acid methyl ester 、 methyl (2SR,3SR)-2-(1'-RS-hydroxybenzyl)-3-hydroxybutanoate 、 (2S,3R)-3-Hydroxy-2-(hydroxy-phenyl-methyl)-butyric acid methyl ester
  参考文献：
  名称：

  Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

  摘要：

  The Eu(III)-catalyzed reaction of alpha-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both ''anti'' diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

  DOI：

  10.1016/s0040-4039(00)91648-4