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Abstract:

The title compound (17) was synthesized by two alternative sequences, starting from D-galactose diacetonide (1) and from methyl 6-O-tosyl-α-D-galac-topyranoside (9). Compound 1 was converted into the 6-bromo-6-deoxy derivative 2 or mesylated to 3. Nucleophilic substitution of the leaving group in 2 and 3 by sodium azide led to the 6-azido-6-deoxy derivative 4, which on treatment with methanol under acidic conditions afforded a mixture of the corresponding methyl β-furanoside (5) and a-pyranoside (6). Methylation of the free hydroxyl groups of 5 and 6 gave the respective per-O-methyl derivatives 7 and 8. In order to maintain the size of the sugar ring during the sequence, compound 8 was alternatively prepared from 9, by acetylation, substitution by azide and per-O-methylation. Hydrolysis of the glycoside followed by oxidation and further 5-O-methylation afforded the 6-azido-6-deoxy carboxylic acid 16 which was converted into 17 (38% overall yield from 9) by hydrogenolysis of the azide function.

Registro:

Documento: Artículo
Título:Synthesis of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid, a key precursor of a stereoregular polyamide
Autor:Zaliz, C.L.R.; Varela, O.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón II Ciudad Universitaria, CIHIDECAR-CONICET, Buenos Aires, 1428, Argentina
Año:2001
Volumen:20
Número:7-8
Página de inicio:689
Página de fin:701
DOI: http://dx.doi.org/10.1081/CAR-100108283
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_v20_n7-8_p689_Zaliz

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Citas:

---------- APA ----------
Zaliz, C.L.R. & Varela, O. (2001) . Synthesis of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid, a key precursor of a stereoregular polyamide. Journal of Carbohydrate Chemistry, 20(7-8), 689-701.
http://dx.doi.org/10.1081/CAR-100108283
---------- CHICAGO ----------
Zaliz, C.L.R., Varela, O. "Synthesis of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid, a key precursor of a stereoregular polyamide" . Journal of Carbohydrate Chemistry 20, no. 7-8 (2001) : 689-701.
http://dx.doi.org/10.1081/CAR-100108283
---------- MLA ----------
Zaliz, C.L.R., Varela, O. "Synthesis of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid, a key precursor of a stereoregular polyamide" . Journal of Carbohydrate Chemistry, vol. 20, no. 7-8, 2001, pp. 689-701.
http://dx.doi.org/10.1081/CAR-100108283
---------- VANCOUVER ----------
Zaliz, C.L.R., Varela, O. Synthesis of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid, a key precursor of a stereoregular polyamide. J. Carbohydr. Chem. 2001;20(7-8):689-701.
http://dx.doi.org/10.1081/CAR-100108283