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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Detalles Bibliográficos
Publicado: 2011
Materias:
Acetonation
Carbohydrate oxidation
Gluconolactone
Hexulosonic acid
Oiodoxybenzoic acid (IBX)
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p237_Kolender
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 paper:paper_1551-701_v2011_n7_p237_Kolender
record_format dspace
spelling paper:paper_1551-701_v2011_n7_p237_Kolender2023-06-08T16:23:02Z A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives 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. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p237_Kolender 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)
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.
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
publishDate 2011
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p237_Kolender
http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p237_Kolender
_version_ 1768541956855562240

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