(S)-2-羟基戊二酸二乙酯 | 55094-99-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-2-羟基戊二酸二乙酯
• 英文名称: (-)-(S)-diethyl 2-hydroxyglutarate
• 英文别名: Diethyl (2S)-2-hydroxypentanedioate
• CAS: 55094-99-0
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: DYLHSDCNOUDICA-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-羟基戊二酸二乙酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran
  参考文献：
  名称：

  通过“环转换”方法合成（S）-3-杂芳基-2-羟基-1-丙基苯甲酸酯

  摘要：

  由L-谷氨酸（1）分5步制备的（S）-5-苯甲酰氧基甲基-3-[（E）-（二甲基氨基）亚甲基]四氢呋喃-2-酮（6）在一步中用作前体（S）-2-羟基-3-杂芳基-1-丙基苯甲酸酯的“环交换”合成13-18，23，24.在6与2-氨基吡啶（21）和2-氨基-4,6的反应中-二甲基嘧啶（22），得到相应的二甲胺取代产物（25、26）。

  DOI：

  10.1002/jhet.5570380610
• 作为产物：
  描述：

  alpha-酮戊二酸 在 Mucor rouxii yeast-like cells 、 Novozym 435 lipase B from Candida antarctica 作用下， 以 正己烷 、 水 为溶剂， 反应 24.0h， 生成 (S)-2-羟基戊二酸二乙酯
  参考文献：
  名称：

  Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid

  摘要：

  An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantionterically pure 3-carboxyalkyl-gamma-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-gamma-butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.013

文献信息

• Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts
  作者：Katalin Balázsik、Kornél Szöri、Béla Török、Mihály Bartók

  DOI：10.1039/b000390p

  日期：——

  The first direct asymmetric synthesis of chiral alkyl 5-oxo-tetrahydrofuran-2-carboxylates (up to 96% ee), which are important building blocks in the synthesis of natural products by heterogeneous cinchona-modified Pt-catalyzed hydrogenation of α-ketoglutaric acid esters and subsequent cyclization of hydroxy esters is described.

  描述了一种直接的不对称合成手性烷基5-氧代四氢呋喃-2-羧酸酯的方法（最高达到96%的对映体过剩），这些化合物是通过异相奎宁修饰的铂催化α-酮戊二酸酯的氢化及随后羟基酯的环化反应中合成天然产物的重要构建块。
• Golding, Bernard T.; Sell, Charles S.; Sellars, Philip J., Journal of the Chemical Society. Perkin transactions II, 1980, p. 961 - 970
  作者：Golding, Bernard T.、Sell, Charles S.、Sellars, Philip J.

  DOI：——

  日期：——
• Katsura, Nippon Kagaku Zasshi, 1956, vol. 77, p. 1789,1791
  作者：Katsura

  DOI：——

  日期：——
• Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
  作者：Sara Drioli、Patrizia Nitti、Giuliana Pitacco、Laura Tossut、Ennio Valentin

  DOI：10.1016/s0957-4166(99)00286-4

  日期：1999.7

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds
  作者：Valéria Riatto、Mauricio Victor、Jaqueline Sousa、Carla Menegola

  DOI：10.21577/0103-5053.20180165

  日期：——

  To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral alpha-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose. the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90%) and good enantioselectivities (60-74%). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.