Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
Autor: | Uhrig, M.L.; Varela, O. |
Filiación: | CIHIDECAR-CONICET, Depto. de Quím. Orgán., Ciudad Universitaria, 1428, Buenos Aires, Argentina
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Palabras clave: | Carbohydrates; Chiral pool; Enones; Olefination; Stereoselective synthesis; Acetylation; Benzene; Carbonates; Complexation; Olefins; Oxidation; Deacetylation; Enantiomers; Enantiospecific synthesis; Olefination; Synthesis (chemical); 2 pyrone derivative; arabinose; article; chemical reaction; chemical structure; chirality; deacetylation; enantiomer; enantioselectivity; olefination; oxidation kinetics; reaction analysis; stereochemistry; structure analysis; synthesis |
Año: | 2005
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Número: | 6
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Página de inicio: | 893
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Página de fin: | 898
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DOI: |
http://dx.doi.org/10.1055/s-2005-861833 |
Título revista: | Synthesis
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Título revista abreviado: | Synthesis
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ISSN: | 00397881
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CODEN: | SYNTB
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CAS: | arabinose, 147-81-9
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n6_p893_Uhrig |
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Citas:
---------- APA ----------
Uhrig, M.L. & Varela, O.
(2005)
. Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose. Synthesis(6), 893-898.
http://dx.doi.org/10.1055/s-2005-861833---------- CHICAGO ----------
Uhrig, M.L., Varela, O.
"Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose"
. Synthesis, no. 6
(2005) : 893-898.
http://dx.doi.org/10.1055/s-2005-861833---------- MLA ----------
Uhrig, M.L., Varela, O.
"Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose"
. Synthesis, no. 6, 2005, pp. 893-898.
http://dx.doi.org/10.1055/s-2005-861833---------- VANCOUVER ----------
Uhrig, M.L., Varela, O. Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose. Synthesis. 2005(6):893-898.
http://dx.doi.org/10.1055/s-2005-861833