(2S,3S)-3-hydroxy-2-(methylthio)-3-phenylpropionic acid methyl ester | 214964-07-5

• 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: (2S,3S)-3-hydroxy-2-(methylthio)-3-phenylpropionic acid methyl ester
• 英文别名: methyl (2S,3S)-3-hydroxy-2-methylsulfanyl-3-phenylpropanoate
• CAS: 214964-07-5
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: NKRXQGDQYYMKGF-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxy-2-(methylthio)-3-phenylpropionic acid methyl ester 在 吡啶 、 phosphate buffer 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2R,3R)-3-hydroxy-2-(methylthio)-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis

  摘要：

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.

  DOI：

  10.1021/jo00002a054
• 作为产物：
  描述：

  苯甲醛 在 吡啶 、 phosphate buffer 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 (2S,3S)-3-hydroxy-2-(methylthio)-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis

  摘要：

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.

  DOI：

  10.1021/jo00002a054

文献信息

• Enantio- and Diastereoselective Aldol-Addition of Chiral Boron Enolates of Carboxylic Acids to Benzaldehyde
  作者：Francesco Fringuelli、Oriana Piermatti、Ferdinando Pizzo

  DOI：10.1021/jo00126a061

  日期：1995.10
• Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis
  作者：Toshiyuki Itoh、Keiko Kuroda、Miki Tomosada、Yumiko Takagi

  DOI：10.1021/jo00002a054

  日期：1991.1

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.