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).
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.
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).
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.
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).
