(2S,3R,4R)-3-methyl-2,4-hexanediol | 1258275-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R)-3-methyl-2,4-hexanediol
• 英文别名: (2S,3R,4R)-3-methylhexane-2,4-diol
• CAS: 1258275-97-6
• 化学式: C₇H₁₆O₂
• 分子量: 132.203
• InChiKey: HSFITJPGVVSHAQ-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (2S,3R)-2-hydroxy-3-methyl-4-hexanone 在 glucose dehydrogenase 、 葡萄糖 、 ketoreductase A₁B 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 2.0h， 以99%的产率得到(2S,3R,4R)-3-methyl-2,4-hexanediol
  参考文献：
  名称：

  Highly diastereoselective synthesis of 2-substituted-1,3-diols catalyzed by ketoreductases

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.09.096

文献信息

• S _N 2 Reactions at Tertiary Carbon Centers in Epoxides
  作者：Yong‐Qiang Zhang、Christina Poppel、Anastasia Panfilova、Fabian Bohle、Stefan Grimme、Andreas Gansäuer

  DOI：10.1002/anie.201702882

  日期：2017.8.7

  Described herein is a novel concept for SN2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why SN2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3‐diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations

  本文描述了在环氧化物中叔碳中心处的S N 2反应而不活化离去基团的新颖概念。量子化学计算表明为什么在这些系统中三级碳中心的S N 2反应正在进行。该反应可以灵活地合成1,3-二醇结构单元，用于天然产物的合成，并具有相对和绝对构型的出色控制。
• 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.
• 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.