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Gallo, C.; Jeroncic, L.O.; Varela, O.; Lederkremer, R.M.D. "Regioselective acylations of aldono-1, 4-lactones" (1993) Journal of Carbohydrate Chemistry. 12(7):841-851
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Abstract:

Partial benzoylation or pivaloylation of D-gulono- 1, 4-lactone (1) with 3.3-3.6 molar equivalents of the acyl chloride afforded 2, 5, 6-tri-O-benzoyl- (3) or 2, 5, 6-tri-O-pivaloyl-D-gulono-1, 4-lactone (5), which were isolated crystalline from the reaction mixture in yields of 54% and 84.5 %, respectively. Similarly, partial pivaloylation of L-mannono-1, 4-lactone (6) gave crystalline 2, 5, 6-tri-O-pivaloyl-L-mannono-1, 4-lactone (9) in 50% yield. Under the same conditions of acylation, D-galactono-1, 4-lactone (11) gave a mixture of products, which were separated by column chromatography. On benzoylation, 2, 3, 5, 6-tetra-O-benzoyl-(12); 2, 5, 6-tri-O-benzoyl- (13); 2, 3, 6-tri-O-benzoyl- (14) and 2, 6-di-O-benzoyl-D-galactono-1, 4-lactone (15) were obtained in 47%, 16.4%, 8%, and 14% yield, respectively. Pivaloylation of 11 afforded 2, 3, 5, 6-tetra-O-pivaloyl- (16), 2, 5, 6-tri-O-pivaloyl-(17), 2, 3, 6-tri-O-pivaloyl (18) and 2, 6-di-O-pivaloyl-D-galactono- 1, 4-lactone (19) in 21.6%, 9.7%, 2.6%, and 30.0%, respectively. © 1993, Taylor & Francis Group, LLC. All rights reserved.

Registro:

Documento: Artículo
Título:Regioselective acylations of aldono-1, 4-lactones
Autor:Gallo, C.; Jeroncic, L.O.; Varela, O.; Lederkremer, R.M.D.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 11. Ciudad Universitana, 1428, Buenos Aires, Argentina
Año:1993
Volumen:12
Número:7
Página de inicio:841
Página de fin:851
DOI: http://dx.doi.org/10.1080/07328309308020099
Título revista:Journal of Carbohydrate Chemistry
Título revista abreviado:J. Carbohydr. Chem.
ISSN:07328303
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07328303_v12_n7_p841_Gallo

Referencias:

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Citas:

---------- APA ----------
Gallo, C., Jeroncic, L.O., Varela, O. & Lederkremer, R.M.D. (1993) . Regioselective acylations of aldono-1, 4-lactones. Journal of Carbohydrate Chemistry, 12(7), 841-851.
http://dx.doi.org/10.1080/07328309308020099
---------- CHICAGO ----------
Gallo, C., Jeroncic, L.O., Varela, O., Lederkremer, R.M.D. "Regioselective acylations of aldono-1, 4-lactones" . Journal of Carbohydrate Chemistry 12, no. 7 (1993) : 841-851.
http://dx.doi.org/10.1080/07328309308020099
---------- MLA ----------
Gallo, C., Jeroncic, L.O., Varela, O., Lederkremer, R.M.D. "Regioselective acylations of aldono-1, 4-lactones" . Journal of Carbohydrate Chemistry, vol. 12, no. 7, 1993, pp. 841-851.
http://dx.doi.org/10.1080/07328309308020099
---------- VANCOUVER ----------
Gallo, C., Jeroncic, L.O., Varela, O., Lederkremer, R.M.D. Regioselective acylations of aldono-1, 4-lactones. J. Carbohydr. Chem. 1993;12(7):841-851.
http://dx.doi.org/10.1080/07328309308020099