(2S,3R)-trans-(4-methoxyphenyl)glycidic acid | 106003-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3R)-trans-(4-methoxyphenyl)glycidic acid
• 英文别名: (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylic acid
• CAS: 106003-21-8
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: CUHUYVNPCQYRLG-BDAKNGLRSA-N

物化性质

• 沸点：
  384.1±42.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-trans-(4-methoxyphenyl)glycidic acid 以 甲苯 为溶剂， 生成 4-甲氧基苯乙醛
  参考文献：
  名称：

  Lipase activity of Lecitase® Ultra: characterization and applications in enantioselective reactions

  摘要：

  The general properties of Lecitase (R) Ultra, a phospholipase manufactured and marketed by Novozymes, Denmark, have been studied after purification by ultrafiltration. The enzyme has a molecular mass of 35 KD, pH-optimum of 8.5, and appears to possess a single active site which exhibits both the lipase and phospholipase activities that increase in the presence of Ca2+ and Mg2+ ions. The enzyme is inhibited by heavy metal ions and surfactants, and does not accept p-nitrophenyl acetate and glycerol triacetate. Substrates, such as glycerol tributyrate and p-nitrophenyl palmitate, esters of N-acetyl-alpha-amino acids and alpha-hydroxy acids are readily accepted. Amino acids with aliphatic residues, such as alanine, isoleucine, and methionine, are hydrolyzed with high enantioselectivity for the L-enantiomer (E > 100), but amino acids with aromatic residues such as phenylalanine and phenylglycine, and esters of alpha-hydroxy acids are hydrolyzed with low enantioselectivity (E = 1-5). Immobilization of the enzyme in a gelatin matrix (gelozyme) leads to a marginal improvement in the enantioselectivity for these substrates. However, a dramatic improvement in enantioselectivity is observed for ethyl 2-hydroxy-4-oxo-4-phenylbutyrate (E value increases from 4.5 to 19.5 with S-selectivity). Similarly, glycidate esters, such as ethyl trans-(+/-)-3-phenyl glycidate and methyl trans-(+/-)-3-(4-methoxyphenyl) glycidate, are selectively hydrolyzed with a remarkable selectivity towards the (2S,3R)-enantiomer providing unreacted (2R,3S)-glycidate esters (ee >99%, conversion 52-55%) by the immobilized enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.012
• 作为产物：
  描述：

  (2R,3S)-rel-3-(4-甲氧基苯基)-2-环氧乙烷羧酸甲酯 在 水 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 (2R, 3S)-(-)-对甲氧苯基缩水甘油酸甲酯 、 (2S,3R)-trans-(4-methoxyphenyl)glycidic acid
  参考文献：
  名称：

  Lipase activity of Lecitase® Ultra: characterization and applications in enantioselective reactions

  摘要：

  The general properties of Lecitase (R) Ultra, a phospholipase manufactured and marketed by Novozymes, Denmark, have been studied after purification by ultrafiltration. The enzyme has a molecular mass of 35 KD, pH-optimum of 8.5, and appears to possess a single active site which exhibits both the lipase and phospholipase activities that increase in the presence of Ca2+ and Mg2+ ions. The enzyme is inhibited by heavy metal ions and surfactants, and does not accept p-nitrophenyl acetate and glycerol triacetate. Substrates, such as glycerol tributyrate and p-nitrophenyl palmitate, esters of N-acetyl-alpha-amino acids and alpha-hydroxy acids are readily accepted. Amino acids with aliphatic residues, such as alanine, isoleucine, and methionine, are hydrolyzed with high enantioselectivity for the L-enantiomer (E > 100), but amino acids with aromatic residues such as phenylalanine and phenylglycine, and esters of alpha-hydroxy acids are hydrolyzed with low enantioselectivity (E = 1-5). Immobilization of the enzyme in a gelatin matrix (gelozyme) leads to a marginal improvement in the enantioselectivity for these substrates. However, a dramatic improvement in enantioselectivity is observed for ethyl 2-hydroxy-4-oxo-4-phenylbutyrate (E value increases from 4.5 to 19.5 with S-selectivity). Similarly, glycidate esters, such as ethyl trans-(+/-)-3-phenyl glycidate and methyl trans-(+/-)-3-(4-methoxyphenyl) glycidate, are selectively hydrolyzed with a remarkable selectivity towards the (2S,3R)-enantiomer providing unreacted (2R,3S)-glycidate esters (ee >99%, conversion 52-55%) by the immobilized enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.012

文献信息

• Process for resolving chiral intermediates used in making calcium channel blockers
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0430544A1

  公开（公告）日：1991-06-05

  This process enables preparation of the preferred (+)-threo enantiomer by resolution of its racemic mixture of a compound of the formula wherein Y1 and Y2 are each independently lower alkyl and R1 is hydrogen or lower alkyl. The compound is treated with a chiral acid (tartaric acid preferred) in an organic solvent (ethanol preferred) to yield the (+)-threo enantiomer, which is then recovered from the reaction mixture. This enantiomer may then be used to produce the preferred (+)-cis enantiomer of certain benzothiazepine cardiovascular agents.

  该工艺可通过解析式中化合物的外消旋混合物，制备优选的(+)-三对映体。 其中 Y1 和 Y2 各自独立地为低级烷基，R1 为氢或低级烷基。在有机溶剂（乙醇为佳）中用手性酸（酒石酸为佳）处理该化合物，生成(+)-三对映体，然后从反应混合物中回收该对映体。这种对映体可用于生产某些苯并硫氮杂卓类心血管药物的(+)-顺式对映体。
• Procédé de préparation du (-) (2R, 3S)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle et de son énantiomère
  申请人：SYNTHELABO

  公开号：EP0453330A1

  公开（公告）日：1991-10-23

  Procédé de préparation du (-)-(2R,3S)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle , caractérisé en ce qu'on prépare d'abord une solution d'un mélange d'énantiomères du trans (±)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle, riche en énantiomère lévogyre, puis on ajoute à la solution un germe cristallin d'énantiomère lévogyre, on laisse cristalliser et on isole les cristaux formés.

  制备(-)-(2R,3S)-2,3-环氧-3-(4-甲氧基苯基)丙酸甲酯的工艺，其特征在于首先制备反式(±)-2、3-环氧-3-(4-甲氧基苯基)甲基丙酸酯的对映体混合物的溶液，然后向该溶液中加入一种反式(±)-2, 3-环氧-3-(4-甲氧基苯基)甲基丙酸酯对映体的种子晶体，使其结晶，并分离出所形成的晶体。
• The enzymic preparation of (2R,3S)-phenyl glycidic acid esters
  作者：Angelo Gentile、Claudio Giordano、Claudio Fuganti、Luca Ghirotto、Stefano Servi

  DOI：10.1021/jo00050a049

  日期：1992.11
• Laffitte, J A; Gancet, C; Soccol, C, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 1, p. 94 - 95
  作者：Laffitte, J A、Gancet, C、Soccol, C

  DOI：——

  日期：——
• PROCESS FOR PREPARING OPTICALLY ACTIVE GLYCIDATE ESTERS
  申请人：SEPRACOR, INC.

  公开号：EP0440723A1

  公开（公告）日：1991-08-14