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Abstract:

Benzoylation of L-rhamnono-1,5-lactone (1) with an excess of benzoyl chloride and pyridine for 16 h afforded 2,4-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone (2). Catalytic hydrogenation of 2 was stereoselective and gave crystalline 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone (3). Reduction of the lactone 3 with disiamylborane afforded 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexopyranose (4) which, on debenzoylation, gave 3,6-dideoxy-L-arabino-hexose (ascarylose) (7) in good overall yield. The sugar was identified as the corresponding alditol (ascarylitol) and by convertion into methyl 3,6-dideoxy-α-L-arabino-hexopyranoside (methyl ascaryloside, 6). © 1979.

Registro:

Documento: Artículo
Título:β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose)
Autor:Varela, O.J.; Cirelli, A.F.; De Lenderkremer, R.M.
Filiación:Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Año:1979
Volumen:70
Número:1
Página de inicio:27
Página de fin:35
DOI: http://dx.doi.org/10.1016/S0008-6215(00)83267-X
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v70_n1_p27_Varela

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Citas:

---------- APA ----------
Varela, O.J., Cirelli, A.F. & De Lenderkremer, R.M. (1979) . β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose). Carbohydrate Research, 70(1), 27-35.
http://dx.doi.org/10.1016/S0008-6215(00)83267-X
---------- CHICAGO ----------
Varela, O.J., Cirelli, A.F., De Lenderkremer, R.M. "β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose)" . Carbohydrate Research 70, no. 1 (1979) : 27-35.
http://dx.doi.org/10.1016/S0008-6215(00)83267-X
---------- MLA ----------
Varela, O.J., Cirelli, A.F., De Lenderkremer, R.M. "β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose)" . Carbohydrate Research, vol. 70, no. 1, 1979, pp. 27-35.
http://dx.doi.org/10.1016/S0008-6215(00)83267-X
---------- VANCOUVER ----------
Varela, O.J., Cirelli, A.F., De Lenderkremer, R.M. β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose). Carbohydr. Res. 1979;70(1):27-35.
http://dx.doi.org/10.1016/S0008-6215(00)83267-X