(S)-solketal butyrate | 119238-14-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-solketal butyrate
• 英文别名: Butyric acid [(4S)-2,2-dimethyl-1,3-dioxolane-4-yl]methyl ester；[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl butanoate
• CAS: 119238-14-1
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: JMMOQNCIYAMRDB-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-solketal butyrate 在 N,N-双(2-羟乙基)-2-氨基乙磺酸 、 esterase from Pseudomonas fluorescens 作用下， 以 水 为溶剂， 生成 (R)-(-)-甘油醇缩丙酮 、 丁酸
  参考文献：
  名称：

  映射的使用比色筛选新的水解酶的底物选择性：从脂肪酶thermocatenulatus芽孢杆菌和蛇口壳piliferum，从酯酶荧光假单胞菌和链霉菌diastatochromogenes

  摘要：

  生物化学和分子生物学的最新进展简化了新型水解酶的发现和制备。尽管这些水解酶可能解决了有机合成中的问题，但测量其选择性（尤其是对映选择性）仍然繁琐且耗时。最近，我们开发了一种比色筛选方法来测量水解酶的对映选择性。在这里，我们应用这种快速筛选方法来绘制四种新型水解酶的底物选择性图：来自嗜热芽孢杆菌的脂肪酶（DSM 730，BTL2）和丝状真菌Ophiostoma piliferum（NRRL 18917，OPL）以及来自两种细菌荧光假单胞菌（Pseudomonas fluorescens（ SIK-W1，酯酶I，PFE）和链霉菌（Tü20，SDE）。我们筛选了29种底物的通用文库和23对对映异构体的手性文库。所有四种水解酶均催化非天然底物的水解，但是与两种酯酶相比，两种脂肪酶接受的底物范围更广。不出所料，这两种脂肪酶偏爱疏水性更高的底物，而两种酯酶则偏爱较小的底物。确认了该酚醛酸酯的一些中等对映选择性反应：BTL2，丁酸酯，E

  DOI：

  10.1016/s0957-4166(01)00072-6
• 作为产物：
  描述：

  丙酮缩甘油 在 吡啶 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-solketal butyrate
  参考文献：
  名称：

  Enzymatic resolution of 2,2-disubstituted-1,3-dioxolane-4-methanol carboxylic esters

  摘要：

  The enantioselectivity of enzymatic hydrolysis of carboxylic esters of various 1,2-ketals of glycerol has been investigated. The influence of the ketal group has been studied. A number of lipases and proteinases have been tested and the best enantioselectivity was obtained with proteinase from Aspergillus oryzae which gave an E-value of 9 with 2,2-dimethyl-1,3-dioxolane-4-methanol butanoate. Variations in the acyl part revealed that butanoyl was optimal. All hydrolysis products have been synthesised in homochiral forms from homochiral starting materials.

  DOI：

  10.1016/s0957-4166(00)82313-7

文献信息

• Lipases Aided Esterification of (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol
  作者：Aurelia Zniszczol、Krzysztof Walczak

  DOI：10.2174/157017861101140113155507

  日期：2014.1.31

  Racemic solketal (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol 1, was treated with carboxylic acids of varying chain length or their vinyl esters in the presence of different lipases. The esterification reaction was carried out in n-hexane or diisopropyl ether as a solvent. The yield of the solketal esters and their enantiopurity were satisfactory, as indicated by gas chromatography using chiral column. Lipases from Rhizopus oryzae and Pseudomonas fluorescence gave the best enantiomeric excess (ee) when the solketal was treated with vinyl butyrate in a solution of diisopropyl ether at room temperature.

  消旋的索克替醛（2,2-二甲基-1,3-二恶烷-4-基）甲醇1，在不同脂肪酶的存在下，与不同链长的羧酸或其乙烯酯反应。酯化反应在正己烷或二异丙基醚中进行。索克替醛酯的产率和它们的手性纯度令人满意，这一点通过使用手性柱的气相色谱法得到了证实。来自米麹霉和荧光假单胞菌的脂肪酶在索克替醛与乙烯丁酸酯在室温下的二异丙基醚溶液中反应时，给出了最佳的对映体过量（ee值）。
• Low-temperature method for enhancement of enantioselectivity in the lipase-catalyzed kinetic resolutions of solketal and some chiral alcohols
  作者：Takashi Sakai、Tetsuo Kishimoto、Yukie Tanaka、Tadashi Ema、Masanori Utaka

  DOI：10.1016/s0040-4039(98)01747-x

  日期：1998.10

  Low-temperature method (−40 °C at best) for enhancement of the enantioselectivity in a lipase-catalyzed transesterification was proved to be widely applicable to primary and secondary alcohols and enabled theoretical prediction of the course of enhancement of the enantioselectivity physicochemically.

  事实证明，在脂肪酶催化的酯交换反应中提高对映选择性的低温方法（最高为-40°C）已广泛适用于伯醇和仲醇，并能够从理论上预测物理化学上对映选择性提高的过程。
• Optically active 1,3-dioxolane-4-methanols. Lipase-catalysed acylation of racemic ketals and diastereomeric acetals
  作者：Eero Vänttinen、Liisa T. Kanerva

  DOI：10.1016/0957-4166(96)00394-1

  日期：1996.10

  The acylation of 13 different 2-mono- or disubstituted 1,3-dioxolane-4-methanols by lipase AK (lipase from Pseudomonas sp.) catalysis in diisopropyl ether has been studied. In the case of monosubstitution, the stereochemical outcome for the acylation of a racemic diastereomeric mixture is considered using graphs which are based on the determined selectivity ratios. The gram-scale separation of the mixture of cis- and trans-1,2-benzylideneglycerols as well as the mixture of 1,2- and 1,3-benzylideneglycerols, through the lipase AK-catalysed acylation has been described. Copyright (C) 1996 Elsevier Science Ltd
• Baer; Fischer, Journal of the American Chemical Society, 1945, vol. 67, p. 2036
  作者：Baer、Fischer

  DOI：——

  日期：——
• Optimized double kinetic resolution for the preparation of (S)-solketal
  作者：Eero Vänttinen、Liisa T Kanerva

  DOI：10.1016/s0957-4166(97)00057-8

  日期：1997.3

  The lipase AK (lipase from Pseudomonas sp.)-catalysed alcoholysis of racemic solketal (2,2-dimethyl-1,3-dioxolane-4-methanol) esters and acylation of solketal in organic solvents proceeded with E=20-25. This enabled the preparation of the more reactive (S)-enantiomer with more than 30% total isolated yield (based on the racemate) and 95% ee by a double kinetic resolution strategy consisting of enzymatic acylation-chemical saponification-enzymatic acylation or enzymatic alcoholysis-enzymatic acylation sequences. Numerical calculations and theoretical plots for the optimal termination conversions for the 1st and 2nd resolution steps as well as for the final yields as the function of E is considered. (C) 1997 Elsevier Science Ltd.