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Abstract:

A practical procedure for the preparation of chiral 2-S-substituted-2H- pyran-3(6H)-ones is described. According to the reaction conditions, 1,5-anhydro-2,3,4-tri-O-acetyl-d-threo-pent-1-enitol (1) reacted with thiophenol under Lewis acid catalysis to afford the polysubstitution product 1,5-anhydro-2,3,4-tri-S-phenyl-2,3,4-trithio-d,l-threo-pent-1-enitol (2) or phenyl 2,4-di-O-acetyl-3-deoxy-1-thio-α- and β-d-glycero-pent-2- enopyranoside (3 and 4, respectively). The iodine-promoted addition of thiophenol or α-toluenethiol to 1 gave (2S)-2-phenylthio-2H-pyran-3(6H)- one (5) or its 2-benzylthio analogue 6, but these products showed low enantiomeric excesses (ee ∼40-60%). However, dihydropyranone 5 with high optical purity (ee >94%) was successfully obtained by treatment of 4 with iodine in acetonitrile. On the other hand, it was established that the benzylthio group of 5 exerts high stereocontrol in reduction and cycloaddition reactions performed on the α,β-unsaturated carbonyl system. © 2005 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Sugar-derived 2-S-substituted-2H-pyran-3(6H)-ones: Synthesis and reactivity
Autor:Capaccio, C.A.I.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Pabellón II, 1428, Buenos Aires, Argentina
Palabras clave:Dihydropyranone; Glycosylations; Iodine; Lewis acids; Thiols; Catalysis; Iodine; Reduction; Substitution reactions; Synthesis (chemical); Dihydropyranone; Glycosylations; Lewis acids; Polysubstitution; Thiols; Sugar (sucrose); 1,5 anhydro 2,3,4 tri o acetyl dextro threo pent 1 enitol; 1,5 anhydro 2,3,4 tri s phenyl 2,3,4 trithio dextro,levo threo pent 1 enitol; 2 benzylthio 2h pyran 3(6h) one; 2 phenylthio 2h pyran pyran 3(6h) one; acetonitrile; alcohol derivative; carbonyl derivative; iodine; Lewis acid; phenyl 2,4 di o acetyl 3 deoxy 1 thio alpha dextro glyceropent 2 enopyranoside; phenyl 2,4 di o acetyl 3 deoxy 1 thio beta dextro glyceropent 2 enopyranoside; pyran derivative; pyranoside; sugar; thiol derivative; thiophenol; unclassified drug; article; catalysis; chirality; cycloaddition; enantiomer; priority journal; stereochemistry; synthesis; Pentoses; Phenols; Pyrans; Stereoisomerism; Sulfhydryl Compounds
Año:2005
Volumen:340
Número:13
Página de inicio:2104
Página de fin:2110
DOI: http://dx.doi.org/10.1016/j.carres.2005.05.024
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:acetonitrile, 75-05-8; iodine, 7553-56-2; thiol derivative, 13940-21-1; thiophenol, 108-98-5; Pentoses; Phenols; Pyrans; Sulfhydryl Compounds; thiophenol, 108-98-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v340_n13_p2104_Capaccio

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Citas:

---------- APA ----------
Capaccio, C.A.I. & Varela, O. (2005) . Sugar-derived 2-S-substituted-2H-pyran-3(6H)-ones: Synthesis and reactivity. Carbohydrate Research, 340(13), 2104-2110.
http://dx.doi.org/10.1016/j.carres.2005.05.024
---------- CHICAGO ----------
Capaccio, C.A.I., Varela, O. "Sugar-derived 2-S-substituted-2H-pyran-3(6H)-ones: Synthesis and reactivity" . Carbohydrate Research 340, no. 13 (2005) : 2104-2110.
http://dx.doi.org/10.1016/j.carres.2005.05.024
---------- MLA ----------
Capaccio, C.A.I., Varela, O. "Sugar-derived 2-S-substituted-2H-pyran-3(6H)-ones: Synthesis and reactivity" . Carbohydrate Research, vol. 340, no. 13, 2005, pp. 2104-2110.
http://dx.doi.org/10.1016/j.carres.2005.05.024
---------- VANCOUVER ----------
Capaccio, C.A.I., Varela, O. Sugar-derived 2-S-substituted-2H-pyran-3(6H)-ones: Synthesis and reactivity. Carbohydr. Res. 2005;340(13):2104-2110.
http://dx.doi.org/10.1016/j.carres.2005.05.024