Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones

5-Acyloxy-5-acyloxymethyl-5,6-dihydro-2-pyrone derivatives (1a, b and 3b and 5-acyloxy-6-methyl-5,6-dihydro-2-pyrone (3a), obtained by acylation of 2-amino-2-deoxy-D-gluconic acid or L-rhamono- and D-glucono-1,5-lactones, react with tin(IV) chloride to give 3-acylamido- and 3-acyloxy-6-acyloxymethyl...

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Detalles Bibliográficos
Autores principales: Nin, Alejandro Pablo, Varela, Oscar José, Muchnik de Lederkremer, Rosa María
Publicado: 1991
Materias:
pyran derivative
article
nuclear magnetic resonance
synthesis
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin
http://hdl.handle.net/20.500.12110/paper_00397881_v_n1_p73_Nin
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00397881_v_n1_p73_Nin
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spelling paper:paper_00397881_v_n1_p73_Nin2023-06-08T15:03:38Z Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones Nin, Alejandro Pablo Varela, Oscar José Muchnik de Lederkremer, Rosa María pyran derivative article nuclear magnetic resonance synthesis 5-Acyloxy-5-acyloxymethyl-5,6-dihydro-2-pyrone derivatives (1a, b and 3b and 5-acyloxy-6-methyl-5,6-dihydro-2-pyrone (3a), obtained by acylation of 2-amino-2-deoxy-D-gluconic acid or L-rhamono- and D-glucono-1,5-lactones, react with tin(IV) chloride to give 3-acylamido- and 3-acyloxy-6-acyloxymethyl-2-pyrones (2a,b and 4b, respectively) and 3-benzoyloxy-6-methyl-2-pyrone (4a), in excellent yield. On prolonged reaction time (5 h), the pyrone 4b underwent substitution of the allylic benzoate by chlorine to afford the corresponding 6-chloromethyl derivative 4c. Fil:Nin, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1991 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin http://hdl.handle.net/20.500.12110/paper_00397881_v_n1_p73_Nin
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic pyran derivative
article
nuclear magnetic resonance
synthesis
spellingShingle pyran derivative
article
nuclear magnetic resonance
synthesis
Nin, Alejandro Pablo
Varela, Oscar José
Muchnik de Lederkremer, Rosa María
Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
topic_facet pyran derivative
article
nuclear magnetic resonance
synthesis
description 5-Acyloxy-5-acyloxymethyl-5,6-dihydro-2-pyrone derivatives (1a, b and 3b and 5-acyloxy-6-methyl-5,6-dihydro-2-pyrone (3a), obtained by acylation of 2-amino-2-deoxy-D-gluconic acid or L-rhamono- and D-glucono-1,5-lactones, react with tin(IV) chloride to give 3-acylamido- and 3-acyloxy-6-acyloxymethyl-2-pyrones (2a,b and 4b, respectively) and 3-benzoyloxy-6-methyl-2-pyrone (4a), in excellent yield. On prolonged reaction time (5 h), the pyrone 4b underwent substitution of the allylic benzoate by chlorine to afford the corresponding 6-chloromethyl derivative 4c.
author Nin, Alejandro Pablo
Varela, Oscar José
Muchnik de Lederkremer, Rosa María
author_facet Nin, Alejandro Pablo
Varela, Oscar José
Muchnik de Lederkremer, Rosa María
author_sort Nin, Alejandro Pablo
title Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
title_short Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
title_full Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
title_fullStr Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
title_full_unstemmed Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
title_sort ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones
publishDate 1991
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin
http://hdl.handle.net/20.500.12110/paper_00397881_v_n1_p73_Nin
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AT varelaoscarjose readyconversionofsugarderived56dihydro2pyronesinto3acyloxyand3acylamido2pyrones
AT muchnikdelederkremerrosamaria readyconversionofsugarderived56dihydro2pyronesinto3acyloxyand3acylamido2pyrones
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