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Abstract:

Hydrogenolysis of 2, 3, 5-tri-O-benzoyl-6-O-trityl-D-galactono-1, 4-lactone (2) gave the corresponding 3-deoxy-D-xyIo-hexono-l, 4-lactone derivative (3), which on treatment with HBr in acetic acid afforded 2, 5-di-O-benzoyl-6-bromo-3, 6-dideoxy-D-xylo-hexono 1, 4-lactone (4). Hydrogenation of 4 led to 3, 6-dideoxy-D-xylo-hexono-1, 4-lactone dibenzoate (6). The overall yield of 6 from D-galactono-1, 4-lactone (1) was about 59%. Alternatively, compound 6 was prepared (67% overall yield from 1) by hydrogenolysis of 6-bromo-6-deoxy-D-galactono-l, 4-lactone tribenzoate (5), obtained by treatment of 2 with HBr in dry dichloromethane. Diisoamylborane reduction of 6 gave an anomeric mixture of 2, 5-di-O-benzoyl-3, 6-dideoxy-a, p-D-xylo-hexofuranose (7), which on O-debenzoylation afforded 3, 6-dideoxy-D-xylo-hexose (abequose, 8) whose tautomeric equilibrium was studied by 13C NMR spectroscopy. Acetylation of 7 gave the 1-O-acetyl derivative (9) mainly in the βanomeric configuration. Tin (IV) chloride promoted glycosylation of 9 with methanol and ethanol afforded stereoselectively methyl (10) and ethyl 2, 5-di-O-benzoyl-3, 6-dideoxy-p-D-xylo-hexofuranoside (11), respectively. © 1991, Taylor & Francis Group, LLC. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose)
Autor:Moradei, O.; Mortier, C.D.; Varela, O.; Lederkremer, R.M.D.
Filiación:Departamento de Quimica Orgánicá, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, 1428 Buenos Aires, Argentina
Año:1991
Volumen:10
Número:3
Página de inicio:469
Página de fin:479
DOI: http://dx.doi.org/10.1080/07328309108543922
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_v10_n3_p469_Moradei

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Citas:

---------- APA ----------
Moradei, O., Mortier, C.D., Varela, O. & Lederkremer, R.M.D. (1991) . Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose). Journal of Carbohydrate Chemistry, 10(3), 469-479.
http://dx.doi.org/10.1080/07328309108543922
---------- CHICAGO ----------
Moradei, O., Mortier, C.D., Varela, O., Lederkremer, R.M.D. "Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose)" . Journal of Carbohydrate Chemistry 10, no. 3 (1991) : 469-479.
http://dx.doi.org/10.1080/07328309108543922
---------- MLA ----------
Moradei, O., Mortier, C.D., Varela, O., Lederkremer, R.M.D. "Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose)" . Journal of Carbohydrate Chemistry, vol. 10, no. 3, 1991, pp. 469-479.
http://dx.doi.org/10.1080/07328309108543922
---------- VANCOUVER ----------
Moradei, O., Mortier, C.D., Varela, O., Lederkremer, R.M.D. Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose). J. Carbohydr. Chem. 1991;10(3):469-479.
http://dx.doi.org/10.1080/07328309108543922