PDF herunterladen
Synthesis 1991; 1991(1): 73-74
DOI: 10.1055/s-1991-26383
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Ready Conversion of Sugar Derived 5,6-Dihydro-2-pyrones into 3-Acyloxy- and 3-Acylamido-2-Pyrones

Alejandro Nin* , Oscar Varela, Rosa M. de Lederkremer
  • *Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 1428 Buenos Aires, Argentina
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
17. September 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

5-Acyloxy-6-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 (5h), the pyrone 4b underwent substitution of the allylic benzoate by chlorine to afford the corresponding 6-chloromethyl derivative 4c.

      >