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Abstract:

The synthesis of crystalline per-0-TBS-β-D-galactofuranose (Aβ) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high β-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved. © 2009 American Chemical Society.

Registro:

Documento: Artículo
Título:Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide
Autor:Baldoni, L.; Marino, C.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Anomeric; Butyldimethylsilyl; Facile synthesis; Galactofuranose; Glycosyl acceptors; In-situ; Protective groups; Simple alcohols; Stereoselectivity; acetal derivative; alcohol derivative; furan derivative; article; glycosylation; iodination; nuclear magnetic resonance; promoter region; silylation; stereochemistry; Carbohydrate Conformation; Galactose; Glycosylation; Hydrocarbons, Iodinated; Organosilicon Compounds; Stereoisomerism
Año:2009
Volumen:74
Número:5
Página de inicio:1994
Página de fin:2003
DOI: http://dx.doi.org/10.1021/jo8025274
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:Galactose, 26566-61-0; Hydrocarbons, Iodinated; Organosilicon Compounds; per-O-tert-butyldimethylsilyl-beta-D-galactofuranose
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v74_n5_p1994_Baldoni

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Citas:

---------- APA ----------
Baldoni, L. & Marino, C. (2009) . Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide. Journal of Organic Chemistry, 74(5), 1994-2003.
http://dx.doi.org/10.1021/jo8025274
---------- CHICAGO ----------
Baldoni, L., Marino, C. "Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide" . Journal of Organic Chemistry 74, no. 5 (2009) : 1994-2003.
http://dx.doi.org/10.1021/jo8025274
---------- MLA ----------
Baldoni, L., Marino, C. "Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide" . Journal of Organic Chemistry, vol. 74, no. 5, 2009, pp. 1994-2003.
http://dx.doi.org/10.1021/jo8025274
---------- VANCOUVER ----------
Baldoni, L., Marino, C. Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide. J. Org. Chem. 2009;74(5):1994-2003.
http://dx.doi.org/10.1021/jo8025274