Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose

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Approaches to the enantioselective synthesis of the useful building blocks (2R)- and (2S)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the 'one-pot' preparation of benzyl 2-O-acetyl-...

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Detalles Bibliográficos
Autor principal: Uhrig, M.L
Otros Autores: Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2005
Acceso en línea:Registro en Scopus
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Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 cas  |a arabinose, 147-81-9 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a SYNTB 
100 1 |a Uhrig, M.L. 
245 1 0 |a Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose 
260 |c 2005 
270 1 0 |m Varela, O.; CIHIDECAR-CONICET, Depto. de Quím. Orgán., Ciudad Universitaria, 1428, Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a Approaches to the enantioselective synthesis of the useful building blocks (2R)- and (2S)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the 'one-pot' preparation of benzyl 2-O-acetyl-arabinopyranoside 3,4-thionocarbonates (7 and 14) from benzyl β-L- or β-D- arabinopyranosides (1 and 13). Trimethylphosphite-promoted olefination, followed by O-deacetylation and oxidation gave the optically pure enantiomeric enones 12 and 17 in about 50% overall yield. © Georg Thieme Verlag Stuttgart.  |l eng 
593 |a CIHIDECAR-CONICET, Depto. de Quím. Orgán., Ciudad Universitaria, 1428, Buenos Aires, Argentina 
690 1 0 |a CARBOHYDRATES 
690 1 0 |a CHIRAL POOL 
690 1 0 |a ENONES 
690 1 0 |a OLEFINATION 
690 1 0 |a STEREOSELECTIVE SYNTHESIS 
690 1 0 |a ACETYLATION 
690 1 0 |a BENZENE 
690 1 0 |a CARBONATES 
690 1 0 |a COMPLEXATION 
690 1 0 |a OLEFINS 
690 1 0 |a OXIDATION 
690 1 0 |a DEACETYLATION 
690 1 0 |a ENANTIOMERS 
690 1 0 |a ENANTIOSPECIFIC SYNTHESIS 
690 1 0 |a OLEFINATION 
690 1 0 |a SYNTHESIS (CHEMICAL) 
690 1 0 |a 2 PYRONE DERIVATIVE 
690 1 0 |a ARABINOSE 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMICAL REACTION 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CHIRALITY 
690 1 0 |a DEACETYLATION 
690 1 0 |a ENANTIOMER 
690 1 0 |a ENANTIOSELECTIVITY 
690 1 0 |a OLEFINATION 
690 1 0 |a OXIDATION KINETICS 
690 1 0 |a REACTION ANALYSIS 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a STRUCTURE ANALYSIS 
690 1 0 |a SYNTHESIS 
700 1 |a Varela, O. 
773 0 |d 2005  |h pp. 893-898  |k n. 6  |p Synthesis  |x 00397881  |w (AR-BaUEN)CENRE-27  |t Synthesis 
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856 4 0 |u https://doi.org/10.1055/s-2005-861833  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00397881_v_n6_p893_Uhrig  |y Handle 
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999 |c 83075 

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