(-)-syn-(3R,1'R)-α-(hydroxyethyl)-γ-butyrolactone | 155321-91-8

• 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: (-)-syn-(3R,1'R)-α-(hydroxyethyl)-γ-butyrolactone
• 英文别名: (3R,1'R)-α-hydroxyethyl-γ-butyrolactone；(3R)-3-[(1R)-1-hydroxyethyl]oxolan-2-one
• CAS: 155321-91-8
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: VADDVPICEYYMOZ-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-syn-(3R,1'R)-α-(hydroxyethyl)-γ-butyrolactone 在 吡啶 作用下， 以 乙醚 为溶剂， 生成 (R)-3-((S)-1-Hydroxy-ethyl)-4-methyl-pentane-1,4-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis and stereochemistry of aleppotrioloside, a naturally occurring glucoside

  摘要：

  The stereochemistry of aleppotrioloside, a naturally occurring glucoside, has been determined as (3S)-3-[(1S)-1-hydroxyethyl]-4-methyl-1,4-pentanediol-1-O-beta-D-glucopyranoside by its synthesis based on two key enzymatic reactions: Pseudomonas fluorescens lipase (PFL) catalyzed enantioselective resolution of an aglycone precursor and transglucosylation of the aglycone by thermophilic beta-glycosidase from Sulfolobus solfataricus.

  DOI：

  10.1016/s0040-4039(00)76233-2
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到(-)-syn-(3R,1'R)-α-(hydroxyethyl)-γ-butyrolactone
  参考文献：
  名称：

  前手性羰基化合物的抗Prelog微生物还原

  摘要：

  从各种生境分离的解脂耶氏酵母菌株在前手性羰基的还原中进行了测试。根据酮1a-e的结构，以不同的产率和对映体过量观察到抗-Prelog还原（R-对映体）。

  DOI：

  10.1016/0040-4020(96)00031-2

文献信息

• New Class of Chiral Diphosphine Ligands for Highly Efficient Transition Metal-Catalyzed Stereoselective Reactions:  The Bis(diphenylphosphino) Five-membered Biheteroaryls
  作者：Tiziana Benincori、Elisabetta Brenna、Franco Sannicolò、Licia Trimarco、Patrizia Antognazza、Edoardo Cesarotti、Francesco Demartin、Tullio Pilati

  DOI：10.1021/jo960211f

  日期：1996.1.1

  esters and in the hydrogenation of olefinic substrates. The optical and chemical yields were comparable with those reported for the same Ru(II)-binap-catalyzed reactions carried out under the same experimental conditions. The 2,2'-bis(diphenylphosphino)-3,3'-bibenzo[b]furan (1c), the oxygenated analogue of bitianp, was found to be configurationally unstable at room temperature. Complete structural X-ray

  描述和合成的新型三类手性（C（2））阻转异构二膦的三个例子，其特征是两个相互连接的五元杂芳族环，阻碍了围绕肛门间键的旋转。光学纯的（+）-和（-）-2,2'-双（二苯基膦基）-4,4'，6,6'-四甲基-3,3'-联苯并[b]噻吩（tetraMe-bitianp）（1a ）和未取代的母体系统（+）-和（-）-双键（1b）。发现它们在100℃下具有光学稳定性，并已成功地用作配体用于Ru（II）催化的α-和β-氧代酯氢化为相应的α-和β-羟基酯以及烯烃的氢化基材。光学和化学产率与在相同实验条件下进行的相同Ru（II）-binap催化反应报道的产率相当。发现2,2'-双（二苯基膦基）-3,3'-联苯并[b]呋喃（1c）（双酚的氧化类似物）在室温下构型不稳定。据报道1a-c的Pd复合物的完整结构X射线阐明。讨论了这些双杂芳族配体相对于经典联芳基体系的优势。
• Access to Enantiopure α-Alkyl-β-hydroxy Esters through Dynamic Kinetic Resolutions Employing Purified/Overexpressed Alcohol Dehydrogenases
  作者：Aníbal Cuetos、Ana Rioz-Martínez、Fabricio R. Bisogno、Barbara Grischek、Iván Lavandera、Gonzalo de Gonzalo、Wolfgang Kroutil、Vicente Gotor

  DOI：10.1002/adsc.201200139

  日期：2012.6.18

  and Ralstonia sp. (RasADH) could also accept bulkier keto esters (‘bulky‐bulky’ substrates). SyADH also provided preferentially syn‐(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti‐(2S,3S) derivatives. With anti‐Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn‐(2S,3R) alcohols were obtained with high conversions and diastereomeric excess

  通过使用纯化或粗制的大肠杆菌过表达的醇脱氢酶（ADHs）的动态动力学拆分（DKR）获得α-烷基-β-羟基酯。ADH-A从R.曲霉，CPADH从近平滑念珠菌从和TesADH T. ethanolicus得到顺式- （2- [R，3小号）具有非常高的选择性为空间位不受阻碍酮（“小体积大的”底物）的衍生物，而的ADH来自S. yanoikuyae（SyADH）和Ralstonia sp。（RasADH）也可以接受更大的酮酯（“大块状”底物）。SyADH还提供了优先顺式- （2- ř，3 S）异构体和RasADH在某些情况下显示出对形成抗-（2 S，3 S）衍生物的良好选择性。与抗作为LBADH这样普雷洛格的ADH从短乳杆菌或从LKADH克菲尔乳杆菌，顺式- （2-小号，3 - [R ）与高转化率和对映体过量在某些情况下，特别是与LBADH得到醇。此外，由于这些底物在热力学上有利于还原，因此可以仅
• Effect of high hydrostatic pressure and high pressure homogenization on the enantioselectivity of microbial reductions
  作者：Giancarlo Fantin、Marco Fogagnolo、Maria Elisabetta Guerzoni、Rosalba Lanciotti、Alessandro Medici、Paola Pedrini、Damiano Rossi

  DOI：10.1016/0957-4166(96)00379-5

  日期：1996.10

  The effect of high hydrostatic pressure and high pressure homogenization on the microbial reductions of the model prochiral ketones 1 a-c is described. Various strains of Saccharomyces cerevisiae and Yarrowia lipolytica are utilized in the reduction and higher enantioselectivities are generally achieved together with lower yields compared with the results obtained at atmospheric pressure. In some cases both increasing yields and inversion of enantioselectivity are reported. The effects of the hydrostatic and the homogenization pressure are also compared with the cell viability. Copyright (C) 1996 Elsevier Science Ltd
• Dynamic kinetic resolution in BINAP—ruthenium(II) catalyzed hydrogenation of 2-substituted 3-oxo carboxylic esters
  作者：M. Kitamura、T. Ohkuma、M. Tokunaga、R. Noyori

  DOI：10.1016/s0957-4166(00)82262-4

  日期：1990.1
• Microbial reduction of α-acetyl-γ-butyrolactone
  作者：Joyce Benzaquem Ribeiro、Livia Maria Andrade de Sousa、Mariana da Volta Soares、Maria da Conceição Klaus V. Ramos、Francisco Radler de Aquino Neto、Carlos Alberto Mansour Fraga、Selma G. Ferreira Leite、Yraima Cordeiro、Octavio A.C. Antunes

  DOI：10.1016/j.tetasy.2006.03.015

  日期：2006.3

  Isomers of alpha-1'-hydroxyethyl-gamma-butyrolactone can be considered as potential GHB receptor ligands designed by the molecular hybridization of GLB 2 and GHV 4. Using Aspergillus niger, Geotrichum candidum, and Kluyveromyces marxianus, it was possible to obtain (+)-(3R,1'S)-alpha-1'-hydroxyethyl-gamma-butyrolactone in good to excellent conversions, diastercoisomeric and enantiomeric excesses. The corresponding enantiomer, (-)-(3S, 1'S)-alpha-1'-hydroxyethyl-gamma-butyrolactone was also produced in good conversion, and diastercoisomeric and enantiomeric excesses using Hansenula sp. (c) 2006 Elsevier Ltd. All rights reserved.