57044-25-4Relevant articles and documents
Silica-supported tantalum catalysts for asymmetric epoxidations of allyl alcohols
Meunier, Damien,Piechaczyk, Arnaud,De Mallmann, Aimery,Basset, Jean-Marie
, p. 3540 - 3542 (1999)
Tantalum good, titanium bad: This appears to be the case for silica- supported catalysts for the asymmetric epoxidation of allyl alcohols. Complexes such as [SiO-Ta(OEt)4] were prepared from silica and [Ta(=CHCMe3)(CH2CMe3)3], and in the presence of a tartrate and an alkyl hydroperoxide, these surface tantalum compounds lead to efficient and convenient catalysts for the asymmetric epoxidation of 2-propen-1-ol (R = H) and trans-2-hexen-1-ol (R = nPr; see reaction).
Enzymatic resolution of (±)-glycidyl butyrate in aqueous media. Strong modulation of the properties of the lipase from Rhizopus oryzae via immobilization techniques
Palomo, Jose M.,Segura, Rosa L.,Fernandez-Lorente, Gloria,Guisan, Jose M.,Fernandez-Lafuente, Roberto
, p. 1157 - 1161 (2004)
The enantioselectivity of the lipase from Rhizopus oryzae for the small yet highly interesting (±)-glycidyl butyrate have been greatly modulated by the use of different immobilization techniques. Thus, the enzyme immobilized by interfacial adsorption on an octyl-agarose support presented a very low enantioselectivity (E=2). This value could be improved up to an E=17 by covalently immobilizing the enzyme on the cyanogen bromide agarose. However, the best results were achieved by immobilizing the enzyme via ionic adsorption on supports coated with dextran sulfate, with an E value of 51 (ee99% at 55% conversion).
Synthesis of enantiomerically pure glycidol via a fully enantioselective lipase-catalyzed resolution
Palomo, Jose M.,Segura, Rosa L.,Mateo, Cesar,Terreni, Marco,Guisan, Jose M.,Fernandez-Lafuente, Roberto
, p. 869 - 874 (2005)
The efficient enzymatic synthesis of enantiopure 2,3-epoxypropanol (glycidol) has been achieved. The racemic glycidyl butyrate was successfully resolved by enzymatic hydrolysis using a strategy that combines different immobilization protocols and different experimental reaction conditions. A new enzyme (25 kDa lipase)-which is a lipase-like enzyme purified from the pancreatic porcine lipase (PPL) extract-immobilized on DEAE-Sepharose was selected as the optimal biocatalyst. The optimal results were obtained at pH 7, 25°C and 10% dioxane using this biocatalyst and a very high enantioselectivity for the enzyme was displayed, obtaining both (R)-(-)-glycidyl butyrate and (R)-(+)-glycidol with enantiomeric excesses >99% (E >100). The hydrolysis of (R)-(-)-glycidyl butyrate produced pure (S)-(-)-glycidol.
Novel applications of chloroperoxidase: Enantioselective oxidation of racemic epoxyalcohols
Kiljunen, Eero,Kanerva, Liisa T.
, p. 3529 - 3535 (1999)
The CPO-catalysed enantioselective oxidations of racemic glycidol and cis-2,3-epoxyhexanol to the corresponding aldehydes were studied using tert- butyl hydroperoxide in the 9:9:1 and 18:1 mixtures of hexane:ethyl acetate:buffer and hexane:buffer, respectively. Temperature and pH (100 mM citrate buffer, pH 4.0-7.0) effects on enantioselectivity in the terms of ee for the less reactive alcohol enantiomers with conversion were studied.
Continuous-Flow Synthesis of (R)-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir
Suveges, Nicolas S.,Rodriguez, Anderson A.,Diederichs, Carla C.,de Souza, Stefania P.,Le?o, Raquel A. C.,Miranda, Leandro S. M.,Horta, Bruno A. C.,Pedraza, Sérgio F.,de Carvalho, Otavio V.,Pais, Karla C.,Terra, José H. C.,de Souza, Rodrigo O. M. A.
supporting information, p. 2931 - 2938 (2018/06/27)
(R)-Propylene carbonate is an important intermediate in the synthesis of tenofovir pro-drugs such as tenofovir alafenamide fumarate (TAF) and tenofovir diisoproyl fumarate (TDF). Independent of the pro-drug type, tenofovir presents a chiral secondary hydroxy derivative, which can be obtained directly from (R)-propylene carbonate. Herein, we report our chemo-enzymatic continuous-flow strategy towards (R)-propylene carbonate starting from a very cheap and renewable raw material, glycerol. We were able to synthesize (R)-propylene carbonate in seven continuous-flow steps, starting from glycerol, in good-to-excellent yields (66–93 %) and excellent selectivity (E > 200).
A high selective (S)-β-hydroxy-γ-butyrolactone simple method for preparing
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Paragraph 0048-0050; 0053-0056; 0065-0067; 0070-0072, (2019/02/04)
The invention relates to a simple and convenient preparation method of highly selective (S)-beta-hydroxy-gamma-butyrolactone. The simple and convenient preparation method comprises the following steps: with allyl alcohol as a starting material, preparing (R)-2, 3-epoxy propanol by virtue of asymmetric epoxidation, and carrying out cyanidation, cyan-hydrolysis and esterification on (R)-2, 3-epoxy propanol to prepare the (S)-beta-hydroxy-gamma-butyrolactone. The simple and convenient preparation method is short in reaction route, easily available in raw material, easy in reaction condition operation, high in reaction selectivity and suitable for industrial production.
Synthesis and enzymatic resolution of racemic 2,3-epoxy propyl esters obtained from glycerol
Araujo, Yara Jaqueline Kerber,Avvari, Naga Prasad,Paiva, Derisvaldo Rosa,De Lima, Dênis Pires,Beatriz, Adilson
supporting information, p. 1696 - 1698 (2015/03/14)
A method is described for the synthesis of (±)-2,3-epoxy propyl esters from glycerol, involving reaction of epichlorohydrin with sodium or potassium salts of carboxylic acids in the presence of TBAB as catalyst, with moderate to excellent yields. Kinetic resolution of glycidyl butyrate by lipase of Thermomyces lanuginosa has been achieved with remarkable enantiomeric excess (ee >99%) using 1,4-dioxane as a co-solvent in pure buffer solution (30 and 50 °C, pH = 7.0).
Substrate stereocontrol in bromine-induced intermolecular cyclization: Asymmetric synthesis of pitavastatin calcium
Chen, Weiqi,Xiong, Fangjun,Liu, Qian,Xu, Lingjun,Wu, Yan,Chen, Fener
, p. 4730 - 4737 (2015/07/27)
A novel approach to synthesize pitavastatin calcium (1), an effective HMG-CoA reductase inhibitor, based on readily available and attractively functionalized (R)-3-chloro-1,2-propanediol is reported. This work highlights an intermolecular diastereoselective bromine-induced cyclization of homoallylic carbonate to meet stereochemical challenges in the synthesis of statins. An efficient route to a new triphenylphosphonium tetrafluoroborate salt of a quinoline core is also presented.
Total Syntheses of Perenniporides
Morita, Masao,Ohmori, Ken,Suzuki, Keisuke
supporting information, p. 5634 - 5637 (2015/12/01)
The total syntheses of perenniporide A (1) and related compounds have been achieved. Starting from 1,3,5-trifluorobenzene (9), difluorodienone 6 was obtained by oxidative dearomatization, which served as a platform for the high-pressure cycloaddition and for the introduction of the C3-methoxy group. The synthesis allowed access to the natural congeners 2 and 3, enabling assignment of the absolute structures of these natural products.
Engineering Homochiral Metal-Organic Frameworks by Spatially Separating 1D Chiral Metal-Peptide Ladders: Tuning the Pore Size for Enantioselective Adsorption
Stylianou, Kyriakos C.,G?mez, Laura,Imaz, Inhar,Verdugo-Escamilla, Crist?bal,Ribas, Xavi,Maspoch, Daniel
supporting information, p. 9964 - 9969 (2015/07/07)
The reaction of the chiral dipeptide glycyl-L(S)-glutamate with CoII ions produces chiral ladders that can be used as rigid 1D building units. Spatial separation of these building units with linkers of different lengths allows the engineering of homochiral porous MOFs with enhanced pore sizes, pore volumes, and surface areas. This strategy enables the synthesis of a family of isoreticular MOFs, in which the pore size dictates the enantioselective adsorption of chiral molecules (in terms of their size and enantiomeric excess).
