(2S)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester
• 英文别名: S-(+)-4-carbossietil-4-butanolide；(S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester；ethyl (S)-(+)-tetrahydro-5-oxo-2-furancarboxylate；(S)-γ-(Ethoxycarbonyl)-γ-butyrolactone；(S)-(+)-γ-carboxy-γ-butyrolactone ethylester；Ethyl (S)-5-oxotetrahydrofuran-2-carboxylate；ethyl (2S)-5-oxooxolane-2-carboxylate
• 化学式: C₇H₁₀O₄
• mdl: MFCD00012088
• 分子量: 158.154
• InChiKey: MJQGWRVDIFBMNW-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 在 sodium tetrahydroborate 、 双氧水 、 sodium carbonate 、 lithium iodide 、 lithium diisopropyl amide 作用下， 以 丙酮 为溶剂， 生成 (+)-eldanolide
  参考文献：
  名称：

  Absolute configuration of eldanolide, the wing gland pheromone of the male African sugar cane borer, Eldana saccharina (Wlk.) syntheses of its (+) and (−) enantiomers.

  摘要：

  DOI：

  10.1016/s0040-4039(00)85570-7
• 作为产物：
  描述：

  alpha-酮戊二酸 在 Mucor rouxii freeze-dried 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 (2S)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester
  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。
• Synthesis of d-amicetose and l-rhodinose from l-glutamic acid
  作者：Giancarlo Berti、Paola Caroti、Giorgio Catelani、Luigi Monti

  DOI：10.1016/0008-6215(83)88353-0

  日期：1983.12

  Abstract l -Glutamic acid has been converted into a separable mixture of d -amicetono- and l -rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2, conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or borane-methyl sulfide. Reduction of the two lactones with di-isobutylaluminium

  摘要通过涉及转化为（S）-γ-羧基-γ-丁内酯（2），转化为2，通过重氮酮途径将2转化为相应的甲基酮，然后用硼氢化锌或硼烷-甲基硫醚选择性还原。用氢化二异丁基铝还原两个内酯得到相应的脱氧糖。尽管制备2的方法有所改进，但该步骤的光学收率仅为约80％，但从氯仿中结晶一次后，其光学纯度提高到96％。随后的步骤仅产生4％的光学纯度损失。
• Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters
  作者：Sara Drioli、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(00)00057-4

  日期：2000.4

  Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned gamma-lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd. All rights reserved.
• PYRENE INTERCALATING NUCLEIC ACIDS WITH A CARBON LINKER
  作者：Michael E. Østergaard、Michael C. Wamberg、Erik B. Pedersen

  DOI：10.1080/15257770.2011.567202

  日期：2011.1

  We have synthesized a carbon linker analogue of INA (oligonucleotides containing insertions of 1-O-(1-pyrenylmethyl)glycerol). Thermal stability studies showed an increase in melting temperature in favor of the carbon linker analogue. We also synthesized a carbon linker analogue with two pyrenes geminally attached. Fluorescence studies of this intercalating nucleic acid with the pyrene moieties inserted as a bulge showed formation of an excimer band. When a mismatch was introduced at the site of the intercalator, an excimer band was formed for the destabilized duplexes whereas an exciplex band was observed when the stability of the duplex was retained.
• Pirillo; Leggeri; Traverso, Farmaco, Edizione Scientifica, 1984, vol. 39, # 5, p. 473 - 476
  作者：Pirillo、Leggeri、Traverso

  DOI：——

  日期：——