(S)-2,4-Dihydroxy-3,3-dimethylbutyronitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2,4-Dihydroxy-3,3-dimethylbutyronitrile
• 英文别名: (S)-2,4-dihydroxy-3,3-dimethylbutylnitrile；(S)-hydroxypivalaldehyde cyanohydrin；(2S)-2,4-dihydroxy-3,3-dimethylbutanenitrile
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: YRISILVEKHMLPL-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (-)-(S)-2,2,5,5-tetramethyl-1,3-dioxane-4-carbonitrile 在 盐酸 、 水 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以95%的产率得到(S)-2,4-Dihydroxy-3,3-dimethylbutyronitrile
  参考文献：
  名称：

  一种用于合成对映体纯氰醇的便捷脱水程序

  摘要：

  从受保护的 α-羟基酰胺开始，氰醇（α-羟基腈）通过三聚氯氰/DMF 脱水以优异的收率获得。该程序的优点是防止外消旋化的极其温和的反应条件。

  DOI：

  10.1055/s-2000-6403

文献信息

• Efficient Biocatalytic Synthesis of (<i>R</i>)-Pantolactone
  作者：Beate Pscheidt、Zhibin Liu、Richard Gaisberger、Manuela Avi、Wolfgang Skranc、Karl Gruber、Herfried Griengl、Anton Glieder

  DOI：10.1002/adsc.200800354

  日期：2008.9.5

  stereoselective cyanohydrin synthesis in 96-well plates was employed in the development of an efficient, pH-stable hydroxynitrile lyase for the conversion of sterically hindered aliphatic aldehydes. Site-saturation mutagenesis (SSM) resulted in a powerful catalyst for the stereoselective conversion of hydroxypivalaldehyde and pivalaldehyde to their corresponding (R)-cyanohydrins (ee >97%) which are used as chiral

  在开发有效的，pH稳定的羟腈裂解酶以转化空间受阻的脂族醛的过程中，在96孔板中筛选了立体选择性氰醇合成。位点饱和诱变（SSM）产生了强大的催化剂，可将羟基新戊醛和新戊醛立体选择性转化为其相应的（R）-氰醇（ee > 97％），用作手性构件（例如，用于生产泛酸）。此外，重新设计帕HNL5基因和通过提高其表达巴斯德毕赤酵母与新的P的帮助AOX1启动子变体和辅助蛋白PDI（蛋白二硫键异构酶）导致当今维生素B 5合成最有效的生物催化剂数量增加。
• Enzyme catalyzed addition of hydrocyanic acid to substituted pivalaldehydes — A novel synthesis of (R)-pantolactone
  作者：Franz Effenberger、Joachim Eichhorn、Jürgen Roos

  DOI：10.1016/0957-4166(94)00384-n

  日期：1995.1

  (R)-Cyanohydrins (R)2b-h are obtained in good optical yields by (R)-oxynitrilase catalyzed enantioselective addition of HCN to beta-substituted pivalaldehydes 1b-h. Under optimized reaction conditions with highly purified (R)-oxynitrilase, hydroxypivalaldehyde (1a) is converted to (R)-2a in satisfactory chemical and optical yields. By acid-catalyzed hydrolysis the cyanohydrins (R)-2a-h cyclize directly to give crude (R)-pantolactone (R)-3 with ee-values of 56-95% which, after recrystallization, go up to greater than or equal to 98%ee in all cases.
• Calcium Pantothenate. Part 2.¹ Optimisation of Oxynitrilase-Catalysed Asymmetric Hydrocyanation of 3-Hydroxy-2,2-dimethylaldehyde:  Synthesis of (<i>R</i>)-Pantolactone
  作者：Ludwik Synoradzki、Tomasz Rowicki、Marek Włostowski

  DOI：10.1021/op050186s

  日期：2006.1.1

  The synthesis of (R)-pantolactone via oxynitrilase-catalysed asymmetric hydrocyanation of 3-hydroxy-2,2-dimethylaldehyde has been investigated. (R)-Oxynitrilases from almonds as well as from apple and plum kernels were employed as catalysts in the form of defatted meal. A number of factors influencing the hydrocyanation process have been studied and the conditions optimised using statistical methods. (R)-Pantolactone with 74% yield and 30% ee has been synthesised.
• R-HNL random variants and their use for preparing optically pure, sterically hindered cyanohydrins
  申请人：DSM IP Assets B.V.

  公开号：EP2465929B1

  公开（公告）日：2015-12-02
• R-HNL RANDOM VARIANTS AND THEIR USE FOR PREPARING OPTICALLY PURE, STERICALLY HINDERED CYANOHYDRINS
  申请人：DSM IP Assets B.V.

  公开号：EP2092060A1

  公开（公告）日：2009-08-26