Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones |
Autor: | Nin, A.; Varela, O.; De Lederkremer, R.M. |
Filiación: | Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon II, 1428 Buenos Aires, Argentina
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Palabras clave: | pyran derivative; article; nuclear magnetic resonance; synthesis |
Año: | 1991
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Número: | 1
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Página de inicio: | 73
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Página de fin: | 74
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Título revista: | Synthesis
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Título revista abreviado: | SYNTHESIS
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ISSN: | 00397881
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CODEN: | SYNTB
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin |
Citas:
---------- APA ----------
Nin, A., Varela, O. & De Lederkremer, R.M.
(1991)
. Ready conversion of sugar derived 5,6-dihydro-2-pyrones into 3-acyloxy- and 3-acylamido-2-pyrones. Synthesis(1), 73-74.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin [ ]
---------- CHICAGO ----------
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"
. Synthesis, no. 1
(1991) : 73-74.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin [ ]
---------- MLA ----------
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"
. Synthesis, no. 1, 1991, pp. 73-74.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin [ ]
---------- VANCOUVER ----------
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. SYNTHESIS. 1991(1):73-74.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n1_p73_Nin [ ]