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Abstract:

High yielding routes for the synthesis of selectively protected derivatives of D- and L-galactonic acids, having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono-1,4-lactones was developed as a key step of the sequence. For example, 6-azido-6-deoxy-L-galactono-1,4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, MeI) to the methyl ester of the 2,3,4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 of L-galactonolactone 1 and isopropylidenation; followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. © 2003 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers
Autor:Romero Zaliz, C.L.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. de Quím. Orgán., Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:6 amino 6 deoxy 2,3,4,5 tetra o methyl dextro galactonic acid; 6 amino 6 deoxy 2,3,4,5 tetra o methyl levo galactonic acid; 6 azido 6 deoxy levo galactono 1,4 lactone; acid; azide; bromine; dimethyl sulfoxide; ester; ester derivative; galactose; lactone derivative; levo galactonolactone; methyl 6 azido 6 deoxy 2,3,4,5 tetra o methyl levo galactonate; methyl group; methyl iodide; polymer; potassium; sodium hydroxide; unclassified drug; article; bromination; chemical analysis; chemical structure; methylation; precursor; priority journal; reaction analysis; structure analysis; synthesis; technique
Año:2003
Volumen:14
Número:17
Página de inicio:2579
Página de fin:2586
DOI: http://dx.doi.org/10.1016/S0957-4166(03)00588-3
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:azide, 12596-60-0, 14343-69-2; bromine, 7726-95-6; dimethyl sulfoxide, 67-68-5; galactose, 26566-61-0, 50855-33-9, 59-23-4; methyl iodide, 74-88-4; potassium, 7440-09-7; sodium hydroxide, 1310-73-2
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v14_n17_p2579_RomeroZaliz

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Citas:

---------- APA ----------
Romero Zaliz, C.L. & Varela, O. (2003) . Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers. Tetrahedron Asymmetry, 14(17), 2579-2586.
http://dx.doi.org/10.1016/S0957-4166(03)00588-3
---------- CHICAGO ----------
Romero Zaliz, C.L., Varela, O. "Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers" . Tetrahedron Asymmetry 14, no. 17 (2003) : 2579-2586.
http://dx.doi.org/10.1016/S0957-4166(03)00588-3
---------- MLA ----------
Romero Zaliz, C.L., Varela, O. "Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers" . Tetrahedron Asymmetry, vol. 14, no. 17, 2003, pp. 2579-2586.
http://dx.doi.org/10.1016/S0957-4166(03)00588-3
---------- VANCOUVER ----------
Romero Zaliz, C.L., Varela, O. Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers. Tetrahedron Asymmetry. 2003;14(17):2579-2586.
http://dx.doi.org/10.1016/S0957-4166(03)00588-3