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Abstract:

The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C- and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with value as glycomimetics or as precursors of glycobiological tools were synthesized. Among them, the synthesis of the isolable 1-galactofuranosylthiol 15 is remarkable, as it paves the way for alternative approaches for S-galactofuranosyl derivatives. © 2012 Elsevier Ltd. All rights reserved.

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Documento: Artículo
Título:Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor
Autor:Baldoni, L.; Marino, C.
Filiación:CIHIDECAR-CONICET, Dpto. de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Buenos Aires (1428), Argentina
Palabras clave:C-Galactofuranosylation; Galactofuranosyl iodide; Per-tert-butyldimethylsilyl-β-d-galactofuranose; S-Galactofuranosylation; Alternative approach; Anomerics; C-Galactofuranosylation; Galactofuranosyl iodide; Glycomimetics; Glycosyl donors; S-Galactofuranosylation; Organic compounds; Synthesis (chemical); Chemical compounds; 1 galactofuranosylthiol derivative; furan derivative; galactofuranoside; galactofuranosyl iodide; iodide; nucleophile; thiol derivative; unclassified drug; article; carbohydrate synthesis; chemical reaction; galactofuranosylation; glycosylation; iodination; priority journal; synthesis; Galactosides; Glycosylation; Halogenation; Magnetic Resonance Spectroscopy; Stereoisomerism; Sulfhydryl Compounds; Trimethylsilyl Compounds
Año:2012
Volumen:362
Página de inicio:70
Página de fin:78
DOI: http://dx.doi.org/10.1016/j.carres.2012.08.021
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:iodide, 20461-54-5; thiol derivative, 13940-21-1; Galactosides; Sulfhydryl Compounds; Trimethylsilyl Compounds; trimethylsilyl iodide
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v362_n_p70_Baldoni

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Citas:

---------- APA ----------
Baldoni, L. & Marino, C. (2012) . Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor. Carbohydrate Research, 362, 70-78.
http://dx.doi.org/10.1016/j.carres.2012.08.021
---------- CHICAGO ----------
Baldoni, L., Marino, C. "Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor" . Carbohydrate Research 362 (2012) : 70-78.
http://dx.doi.org/10.1016/j.carres.2012.08.021
---------- MLA ----------
Baldoni, L., Marino, C. "Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor" . Carbohydrate Research, vol. 362, 2012, pp. 70-78.
http://dx.doi.org/10.1016/j.carres.2012.08.021
---------- VANCOUVER ----------
Baldoni, L., Marino, C. Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor. Carbohydr. Res. 2012;362:70-78.
http://dx.doi.org/10.1016/j.carres.2012.08.021