(3S,6S)-3-(1-Hydroxyethyl)tetrahydrofuran-2-one | 1003-88-9

• 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: (3S,6S)-3-(1-Hydroxyethyl)tetrahydrofuran-2-one
• 英文别名: 3S-(1'S-hydroxyethyl)-γ-butyrolactone；(3S)-3-[(1S)-1-hydroxyethyl]oxolan-2-one
• CAS: 1003-88-9；75612-67-8；75612-69-0；130549-61-0；142034-05-7；142034-04-6
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: VADDVPICEYYMOZ-WHFBIAKZSA-N

物化性质

• 沸点：
  76-77 °C(Press: 0.1 Torr)
• 密度：
  1.189±0.06 g/cm3(Predicted)

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：

  (3S,6S)-3-(1-Hydroxyethyl)tetrahydrofuran-2-one 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 反应 5.0h， 生成 2-((4S,5R)-2,2,4-Trimethyl-[1,3]dioxan-5-yl)-ethanol
  参考文献：
  名称：

  Synthesis of Chiral Lactones and Triols from a-Acetyl-g-butyrolactones by Use of Bakes's YEast

  摘要：

  Chiral hydroxyethyllactones prepared from alpha-acetyl-gamma-butyrolactones by fermenting with baker's yeast are reduced to give chiral triols.

  DOI：

  10.3987/com-91-s53
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (3S,6S)-3-(1-Hydroxyethyl)tetrahydrofuran-2-one
  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

文献信息

• 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
• Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones
  作者：Kazushi Mashima、Koh-hei Kusano、Naomasa Sato、Yoh-ichi Matsumura、Kyoko Nozaki、Hidenori Kumobayashi、Noboru Sayo、Yoji Hori、Takero Ishizaki

  DOI：10.1021/jo00090a026

  日期：1994.6

  Cationic ruthenium-BINAP complexes 5, 7, and 10 of the formula [RuX((S)-BINAP) (arene)]Y, where X = Cl, Br, I; Y = Cl, Br, I, BF4, B(C6H5)(4); arene = benzene, p-cymene, ethyl benzoate, and their enantiomers have been prepared by the reaction of arene-ruthenium halide complexes 4, 6, and 9 with (S)-BINAP or (R)-BINAP. Structures of the complexes were established by spectroscopy, conductivity, and a single-crystal X-ray analysis (5d: orthorhombic, P2(1)2(1)2; a 20.141(2) Angstrom, b = 18.504(1) Angstrom, c 12.241(1) Angstrom V = 4562.0(7) Angstrom(3), Z = 4, R = 0.078 for unique 4177 reflections). BINAP derivatives with various substituents at the para and meta positions of four phenyl rings on phosphorus atoms and their cationic Ru(II) complexes have also been synthesized. These BINAP-Ru(II) complexes have been used as catalysts for the asymmetric hydrogenation of various unsaturated organic compounds such as alpha- and beta-keto esters, allylic alcohols, and alpha,beta-unsaturated carboxylic acids in excellent diastereo- and/or enantioselectivities. Catalytic activities and stereoselectivities depend highly on reaction conditions such as solvent, temperature, and additives. Variation of halogen ligands bound to ruthenium atom and substituents on four phenyl rings of BINAP also have exerted remarkable effects on the efficiency of the catalysis. Asymmetric hydrogenation of methyl (+/-)-2-(benzamidomethyl)-3-oxobutanoate catalyzed by the species derived from 9c and 3,5((t)Bu)(2)-BINAP afforded the corresponding syn-(2S,3R)-17 in 98% de and 99% ee.
• 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
• Synthesis of homochiral syn- andanti-α-(hydroxyethyl)-γ-butyrolactones via microbial reduction
  作者：Giancarlo Fantin、Marco Fogagnolo、Paolo Giovannini、Alessandro Medici、Edoardo Pagnotta、Paola Pedrini、Antonio Trincone

  DOI：10.1016/0957-4166(94)80067-7

  日期：1994.9

  Various yeast and mould strains were tested in the reduction of alpha-acetyl-gamma-butyrolactone. syn-(3R,1'R)-alpha-(Hydroxyethyl)-gamma-butyrolactone 2 and anti-(3R,1'S) isomer 3 were obtained enantiomerically pure. Good enantiomeric excesses are described for the corresponding enantiomers.