A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives

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-iodoxybe...

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Autores principales:	Kolender, A.A., Puenzo, S.C.P., Varela, O.
Formato:	JOUR
Materias:	Acetonation Carbohydrate oxidation Gluconolactone Hexulosonic acid Oiodoxybenzoic acid (IBX)
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p237_Kolender
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_1551-701_v2011_n7_p237_Kolender
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spelling	todo:paper_1551-701_v2011_n7_p237_Kolender2023-10-03T16:25:19Z A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives Kolender, A.A. Puenzo, S.C.P. Varela, O. Acetonation Carbohydrate oxidation Gluconolactone Hexulosonic acid Oiodoxybenzoic acid (IBX) 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p237_Kolender
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Acetonation Carbohydrate oxidation Gluconolactone Hexulosonic acid Oiodoxybenzoic acid (IBX)
spellingShingle	Acetonation Carbohydrate oxidation Gluconolactone Hexulosonic acid Oiodoxybenzoic acid (IBX) 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
topic_facet	Acetonation Carbohydrate oxidation Gluconolactone Hexulosonic acid Oiodoxybenzoic acid (IBX)
description	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.
format	JOUR
author	Kolender, A.A. Puenzo, S.C.P. Varela, O.
author_facet	Kolender, A.A. Puenzo, S.C.P. Varela, O.
author_sort	Kolender, A.A.
title	A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
title_short	A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
title_full	A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
title_fullStr	A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
title_full_unstemmed	A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
title_sort	convenient synthesis of hexulosonic acids by ibx mediated oxidation of d-glucono-1,5-lactone derivatives
url	http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p237_Kolender
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A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives

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