(–)-(R)-diethyl 2-hydroxyglutarate | 69556-79-2

• 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: (–)-(R)-diethyl 2-hydroxyglutarate
• 英文别名: (R)-(+)-α-Hydroxyglutarsaeurediethylester；diethyl (2R)-2-hydroxypentanedioate
• CAS: 69556-79-2
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: DYLHSDCNOUDICA-SSDOTTSWSA-N

物化性质

• 沸点：
  291.8±25.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

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：

  (–)-(R)-diethyl 2-hydroxyglutarate 在 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 生成 (R)-(-)-γ-乙氧羰基-γ-丁内酯
  参考文献：
  名称：

  Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts

  摘要：

  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。

  DOI：

  10.1039/b000390p
• 作为产物：
  描述：

  alpha-酮戊二酸 在 cliona varians 、 aspartic acid anion II 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 144.0h， 生成 (S)-2-羟基戊二酸二乙酯 、 (–)-(R)-diethyl 2-hydroxyglutarate
  参考文献：
  名称：

  Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds

  摘要：

  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.

  DOI：

  10.21577/0103-5053.20180165

文献信息

• Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration
  作者：Uzi Ravid、Robert M. Silverstein、Leverett R. Smith

  DOI：10.1016/0040-4020(78)80164-1

  日期：1978.1

  alkenyl)-γ-lactones of known absolute configuration were synthesized from glutamic acid enantiomers. The key step is selective tosylate displacement rather than ring opening of the lactone tosylate (7→1) by lithium dialkylcuprate or dialkenylcuprate. The enantiomeric purity of synthesized γ-caprolactone was confirmed within the limitations of Pirkle's chiral solvating agent. The enantiomers of synthesized

  由谷氨酸对映异构体合成了几种已知绝对构型的4-烷基（或烯基）-γ-内酯的高纯度对映异构体。关键步骤是通过二烷基铜酸锂或二烯基铜酸锂选择性取代甲苯磺酸酯而不是将内酯甲苯磺酸酯（7 → 1）开环。在Pirkle手性溶剂化剂的限制下，确认了合成的γ-己内酯的对映体纯度。合成的（Z）-6-十二烯-4-油化物的对映体用于确定从黑尾鹿中分离出的信息素的对映体组成。
• 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。
• 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.