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Abstract:

The oxidation of the free hydroxyl group of methyl 3,4:5,6-di-O- isopropylidene-D-gluconate 2 or its 2,3:5,6-di-O-isopropylidene analogue 3, the products of acetonation of D-glucono-1,5-lactone 1, has been attempted by alternative procedures. The oxidation of OH-2 in 2, or OH-4 in 3, with o-iodoxybenzoic acid (IBX) took place to afford the respective 2-keto 4 and 4-keto 7 derivatives in almost quantitative yields. In contrast, the oxidations with pyridinium dichromate were unsuccessful, and those using dimethylsulfoxide?acetic anhydride afforded low yields of 4 or 7. Selective removal of the isopropylidene groups in 4 or 7 with 88% aqueous acetic acid afforded, respectively, the methyl esters 5 or 8; whereas treatment with aqueous trifluoroacetic acid led to the free hexulosonic acids 6 or 9. The tautomeric preferences for the oxidation products 4 and 7, and their derivatives, have been established by 13C NMR spectroscopy. © ARKAT-USA, Inc.

Registro:

Documento: Artículo
Título:A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
Autor:Kolender, A.A.; Puenzo, S.C.P.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Acetonation; Carbohydrate oxidation; Gluconolactone; Hexulosonic acid; Oiodoxybenzoic acid (IBX)
Año:2011
Volumen:2011
Número:7
Página de inicio:237
Página de fin:244
DOI: http://dx.doi.org/10.3998/ark.5550190.0012.720
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:1551-701
CODEN:AGFUA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p237_Kolender

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Citas:

---------- APA ----------
Kolender, A.A., Puenzo, S.C.P. & Varela, O. (2011) . A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives. Arkivoc, 2011(7), 237-244.
http://dx.doi.org/10.3998/ark.5550190.0012.720
---------- CHICAGO ----------
Kolender, A.A., Puenzo, S.C.P., Varela, O. "A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives" . Arkivoc 2011, no. 7 (2011) : 237-244.
http://dx.doi.org/10.3998/ark.5550190.0012.720
---------- MLA ----------
Kolender, A.A., Puenzo, S.C.P., Varela, O. "A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives" . Arkivoc, vol. 2011, no. 7, 2011, pp. 237-244.
http://dx.doi.org/10.3998/ark.5550190.0012.720
---------- VANCOUVER ----------
Kolender, A.A., Puenzo, S.C.P., Varela, O. A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives. Arkivoc. 2011;2011(7):237-244.
http://dx.doi.org/10.3998/ark.5550190.0012.720