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Abstract:

3,4-Di-O-benzyl-1-O-methyl-L-galactitol (3) has been synthesized in a seven step sequence starting from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4). The synthesis involves the methyllation of HO-6 of 4, followed by methanolysis to the mixture of the corresponding methyl 6-O-methyl-α-D-galactopyranoside (6, major product) and the β-furanoside analog (8). Compound 6 was converted into the 3,4-O-isopropylidene derivative 9, and the free HO-group was protected as the methoxyethoxymethyl (MEM) ether. Chemoselective removal of the acetonide by hydrolysis, followed by benzylation gave the methyl 3,4-di-O-benzyl-2-O-methoxyethoxymethyl-6-O-methyl-α-D-galactopyranoside (12). Simultaneous acid hydrolysis of the methyl glycoside and MEM group of 12 led to 13, which was then reduced with sodium borohydride to the target molecule 3.

Registro:

Documento: Artículo
Título:Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a Key Precursor of the C33-C37 Fragment of Calyculins
Autor:Cironi, P.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. de Quim. Orgánica, Ciudad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:Calyculins; Galactose diacetonide; L-galactitol derivative; Marine sponge; Secondary metabolites
Año:2001
Volumen:12
Número:5
Página de inicio:667
Página de fin:672
DOI: http://dx.doi.org/10.1590/S0103-50532001000500010
Título revista:Journal of the Brazilian Chemical Society
Título revista abreviado:J. Braz. Chem. Soc.
ISSN:01035053
CODEN:JOCSE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01035053_v12_n5_p667_Cironi

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Citas:

---------- APA ----------
Cironi, P. & Varela, O. (2001) . Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a Key Precursor of the C33-C37 Fragment of Calyculins. Journal of the Brazilian Chemical Society, 12(5), 667-672.
http://dx.doi.org/10.1590/S0103-50532001000500010
---------- CHICAGO ----------
Cironi, P., Varela, O. "Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a Key Precursor of the C33-C37 Fragment of Calyculins" . Journal of the Brazilian Chemical Society 12, no. 5 (2001) : 667-672.
http://dx.doi.org/10.1590/S0103-50532001000500010
---------- MLA ----------
Cironi, P., Varela, O. "Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a Key Precursor of the C33-C37 Fragment of Calyculins" . Journal of the Brazilian Chemical Society, vol. 12, no. 5, 2001, pp. 667-672.
http://dx.doi.org/10.1590/S0103-50532001000500010
---------- VANCOUVER ----------
Cironi, P., Varela, O. Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a Key Precursor of the C33-C37 Fragment of Calyculins. J. Braz. Chem. Soc. 2001;12(5):667-672.
http://dx.doi.org/10.1590/S0103-50532001000500010