(2S,4S)-3-allyl-2,4-pentanediol | 1258275-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S)-3-allyl-2,4-pentanediol
• 英文别名: (2S,4S)-3-prop-2-enylpentane-2,4-diol
• CAS: 1258275-99-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: FVYIFLDUMIWMKW-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-烯丙基戊烷-2,4-二酮 在 glucose dehydrogenase 、 葡萄糖 、 ketoreductase-108 、 还原型辅酶II(NADPH)四钠盐 、 ketoreductase-111 作用下， 反应 48.0h， 以92%的产率得到(2S,4S)-3-allyl-2,4-pentanediol
  参考文献：
  名称：

  A Two-Step, One-Pot Enzymatic Synthesis of 2-Substituted 1,3-Diols

  摘要：

  A biocatalytic cascade reaction was designed for the stereoselective synthesis of optically pure 2-alkyl-1,3-diols employing two enzymes. The cascade process consists of two consecutive steps: a stereoselective diketone reduction and a hydroxy ketone reduction. Chiral diols were formed by the addition of ketoreductases in the same vessel, in high stereoselectivity and chemical yield, without the isolation of the intermediate beta-hydroxy ketones.

  DOI：

  10.1021/jo101519t

文献信息

• Highly diastereoselective synthesis of 2-substituted-1,3-diols catalyzed by ketoreductases
  作者：Dimitris Kalaitzakis、Ioulia Smonou

  DOI：10.1016/j.tet.2010.09.096

  日期：2010.11

  The stereoselective reduction of alpha-substituted-beta-hydroxy ketones for the preparation of the corresponding optically pure 2-monosubstituted or 2-disubstituted-1,3-diols is described. These transformations proceed in high optical purities and yields. Ketoreductases were able to catalyze the formation of either the syn or the anti diol, depending on the enzyme. By replacing the a-alkyl substituent for an OAc moiety, in low conversion time (<= 24 h), ketoreductases catalyzed the formation of the OAc-protected 1,2,3-triol, in high yield and with high optical purity (>99% de, >99% ee). This is a simple and highly stereoselective method for the synthesis of different diastereomers of chiral diols. (C) 2010 Elsevier Ltd. All rights reserved.
• A Two-Step, One-Pot Enzymatic Synthesis of 2-Substituted 1,3-Diols
  作者：Dimitris Kalaitzakis、Ioulia Smonou

  DOI：10.1021/jo101519t

  日期：2010.12.17

  A biocatalytic cascade reaction was designed for the stereoselective synthesis of optically pure 2-alkyl-1,3-diols employing two enzymes. The cascade process consists of two consecutive steps: a stereoselective diketone reduction and a hydroxy ketone reduction. Chiral diols were formed by the addition of ketoreductases in the same vessel, in high stereoselectivity and chemical yield, without the isolation of the intermediate beta-hydroxy ketones.