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Di Nardo, C.; Jeroncic, L.O.; De Lederkremer, R.M.; Varela, O. "A carbohydrate approach to the enantioselective synthesis of 1,3-polyols" (1996) Journal of Organic Chemistry. 61(12):4007-4013
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Abstract:

Treatment of per-O-benzoyl-D-glycero-D-gulo-heptono-1,4-lactone (2) with tertiary amines afforded selectively and with good yields the (5H)-furan-2-one derivatives 3, 4, and 5, formed by controlled elimination of one, two, or three molecules of benzoic acid, respectively. The stereochemistry for the exocyclic double bonds of 4 and 5 was determined by means of NMR techniques. Particularly, the furanone 4 was obtained from 2 (∼90% yield) as a mixture of the E and Z diastereoisomers, which were separated by column chromatography or, more efficiently, by HPLC. The catalytic hydrogenation of compounds 4-E and 4-Z took place diastereoselectively, due to the chiral induction of the stereocenter located in the lateral chain. Thus, hydrogenation of 4-E led to a mixture of the 4,5-dihydro-(3H)-furan-2-ones having 3R,5S,2′S (D-xylo, 6) and 3S,5R,2′S (D-arabino, 7) configurations, with 6 as the major product; whereas the 4-Z isomer gave the same mixture, but being 7 preponderant. On hydrogenation of the original 4-E / Z mixture, compound 6 was obtained pure after recrystallization. O-Debenzoylation of 6 gave 9, which was reduced with NaBH4 to the 3,5-dideoxy-meso-xylo-heptitol (11). The peracetate (12) and perbenzoate (13) of the latter were prepared, and the 1-(tert-butyldiphenylsilyl)oxy derivative (16) was also synthesized via the 3′-(silyloxy)-4,5-dihydro-(3H)-furan-2-one 14. Chemoselective reduction of the lactone function of 6 with diisoamylborane gave the 2,5,6-tri-O-benzoyl-3,6-dideoxy-D-xylo-heptofuranose (17). The 3,5-dideoxy-D-arabino-heptitol (18), a diastereoisomer of 11, was also isolated and characterized.

Registro:

Documento: Artículo
Título:A carbohydrate approach to the enantioselective synthesis of 1,3-polyols
Autor:Di Nardo, C.; Jeroncic, L.O.; De Lederkremer, R.M.; Varela, O.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Pabellón II, 1428, Buenos Aires, Argentina
Año:1996
Volumen:61
Número:12
Página de inicio:4007
Página de fin:4013
DOI: http://dx.doi.org/10.1021/jo960042z
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v61_n12_p4007_DiNardo

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Citas:

---------- APA ----------
Di Nardo, C., Jeroncic, L.O., De Lederkremer, R.M. & Varela, O. (1996) . A carbohydrate approach to the enantioselective synthesis of 1,3-polyols. Journal of Organic Chemistry, 61(12), 4007-4013.
http://dx.doi.org/10.1021/jo960042z
---------- CHICAGO ----------
Di Nardo, C., Jeroncic, L.O., De Lederkremer, R.M., Varela, O. "A carbohydrate approach to the enantioselective synthesis of 1,3-polyols" . Journal of Organic Chemistry 61, no. 12 (1996) : 4007-4013.
http://dx.doi.org/10.1021/jo960042z
---------- MLA ----------
Di Nardo, C., Jeroncic, L.O., De Lederkremer, R.M., Varela, O. "A carbohydrate approach to the enantioselective synthesis of 1,3-polyols" . Journal of Organic Chemistry, vol. 61, no. 12, 1996, pp. 4007-4013.
http://dx.doi.org/10.1021/jo960042z
---------- VANCOUVER ----------
Di Nardo, C., Jeroncic, L.O., De Lederkremer, R.M., Varela, O. A carbohydrate approach to the enantioselective synthesis of 1,3-polyols. J. Org. Chem. 1996;61(12):4007-4013.
http://dx.doi.org/10.1021/jo960042z