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, A., Varela, O., De Lederkremer, R.M.
Formato:	JOUR
Materias:	pyran derivative article nuclear magnetic resonance synthesis
Acceso en línea:	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	todo:paper_00397881_v_n1_p73_Nin
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spelling	todo:paper_00397881_v_n1_p73_Nin2023-10-03T14:49:54Z Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones Nin, A. Varela, O. De Lederkremer, R.M. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, A. Varela, O. De Lederkremer, R.M. 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.
format	JOUR
author	Nin, A. Varela, O. De Lederkremer, R.M.
author_facet	Nin, A. Varela, O. De Lederkremer, R.M.
author_sort	Nin, A.
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
url	http://hdl.handle.net/20.500.12110/paper_00397881_v_n1_p73_Nin
work_keys_str_mv	AT nina readyconversionofsugarderived56dihydro2pyronesinto3acyloxyand3acylamido2pyrones AT varelao readyconversionofsugarderived56dihydro2pyronesinto3acyloxyand3acylamido2pyrones AT delederkremerrm readyconversionofsugarderived56dihydro2pyronesinto3acyloxyand3acylamido2pyrones
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Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones

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