55094-99-0Relevant articles and documents
Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds
Riatto, Valéria B.,Victor, Mauricio M.,Sousa, Jaqueline F.,Menegola, Carla
, p. 149 - 157 (2018/12/13)
To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral α-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90percent) and good enantioselectivities (60-74percent). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.
Synthesis of (S)-3-heteroaryl-2-hydroxy-1-propyl benzoates by 'ring switching' methodology
Mihelic, Damjana,Jakse, Renata,Svete, Jurij,Stanovnik, Branko,Grdadolnik, Simona Golic
, p. 1307 - 1312 (2007/10/03)
(S)-5-Benzoyloxymethyl-3-[(E)-(dimethylamino)methylidene]tetrahydrofuran-2- one (6), prepared in 5 steps from L-glutamic acid (1), was used as precursor in a one step 'ring switching' synthesis of (S)-2-hydroxy-3-heteroaryl-1-propyl benzoates 13-18, 23, 24. In the reaction of 6 with 2-aminopyridine (21) and 2-amino-4,6-dimethylpyrimidine (22) the corresponding dimethylamine substitution products (25, 26) were obtained.
Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
Drioli, Sara,Nitti, Patrizia,Pitacco, Giuliana,Tossut, Laura,Valentin, Ennio
, p. 2713 - 2728 (2007/10/03)
Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.