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Abstract:

Per-O-tert-butyldimethylsilyl-α,β-d-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-β-d- galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-α-d-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (3T4 and 4TO) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents. © 2010 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate
Autor:Baldoni, L.; Stortz, C.A.; Marino, C.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Conformational analysis; Cyclic thiocarbamate; Galactofuranosyl isothiocyanate; Glycosyl iodide; Molecular modelling; Conformational analysis; Cyclic thiocarbamate; Galactofuranosyl isothiocyanate; Glycosyl iodide; Molecular modelling; Glycosylation; Molecular modeling; Sugar (sucrose); Synthesis (chemical); Conformations; 1,2 cis fused bicyclic alpha galactofuranosyl thiocarbamic acid; isothiocyanic acid derivative; per o tert butyldimethylsilyl beta galactofuranosyl isothiocyanic acid; thiocarbamic acid derivative; thiocyanate potassium; unclassified drug; article; conformation; controlled study; molecular model; priority journal; proton nuclear magnetic resonance; silylation; synthesis; Galactose; Isothiocyanates; Models, Molecular; Molecular Conformation; Organosilicon Compounds; Oxazoles; Thiocarbamates
Año:2011
Volumen:346
Número:2
Página de inicio:191
Página de fin:196
DOI: http://dx.doi.org/10.1016/j.carres.2010.11.013
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:thiocyanate potassium, 333-20-0; Galactose, 26566-61-0; Isothiocyanates; Organosilicon Compounds; Oxazoles; Thiocarbamates
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n2_p191_Baldoni

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Citas:

---------- APA ----------
Baldoni, L., Stortz, C.A. & Marino, C. (2011) . Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate. Carbohydrate Research, 346(2), 191-196.
http://dx.doi.org/10.1016/j.carres.2010.11.013
---------- CHICAGO ----------
Baldoni, L., Stortz, C.A., Marino, C. "Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate" . Carbohydrate Research 346, no. 2 (2011) : 191-196.
http://dx.doi.org/10.1016/j.carres.2010.11.013
---------- MLA ----------
Baldoni, L., Stortz, C.A., Marino, C. "Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate" . Carbohydrate Research, vol. 346, no. 2, 2011, pp. 191-196.
http://dx.doi.org/10.1016/j.carres.2010.11.013
---------- VANCOUVER ----------
Baldoni, L., Stortz, C.A., Marino, C. Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate. Carbohydr. Res. 2011;346(2):191-196.
http://dx.doi.org/10.1016/j.carres.2010.11.013