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Abstract:

An assessment of the relative O-3/O-4 reactivities of both α- and β-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a d-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. © 2013 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
Autor:Della Felice, F.; Rúveda, E.A.; Stortz, C.A.; Colombo, M.I.
Filiación:Instituto de Química Rosario (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina
Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pab. 2, 1428 Buenos Aires, Argentina
Palabras clave:Glucosamine; Glycosylation; Benzyl group; Glycosyl donors; Methyl glycosides; Esterification; carbonyl derivative; disaccharide; glucopyranoside; glucosamine derivative; glycoside; hexosamine; hydroxyl group; acetylation; article; carbohydrate analysis; conformation; glycosylation; hydrogen bond; nucleophilicity; priority journal; stereochemistry; Carbohydrate Conformation; Glycosylation; Hexosamines; Oxygen; Stereoisomerism; Substrate Specificity
Año:2013
Volumen:380
Página de inicio:167
Página de fin:173
DOI: http://dx.doi.org/10.1016/j.carres.2013.08.002
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v380_n_p167_DellaFelice

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Citas:

---------- APA ----------
Della Felice, F., Rúveda, E.A., Stortz, C.A. & Colombo, M.I. (2013) . Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor. Carbohydrate Research, 380, 167-173.
http://dx.doi.org/10.1016/j.carres.2013.08.002
---------- CHICAGO ----------
Della Felice, F., Rúveda, E.A., Stortz, C.A., Colombo, M.I. "Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor" . Carbohydrate Research 380 (2013) : 167-173.
http://dx.doi.org/10.1016/j.carres.2013.08.002
---------- MLA ----------
Della Felice, F., Rúveda, E.A., Stortz, C.A., Colombo, M.I. "Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor" . Carbohydrate Research, vol. 380, 2013, pp. 167-173.
http://dx.doi.org/10.1016/j.carres.2013.08.002
---------- VANCOUVER ----------
Della Felice, F., Rúveda, E.A., Stortz, C.A., Colombo, M.I. Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor. Carbohydr. Res. 2013;380:167-173.
http://dx.doi.org/10.1016/j.carres.2013.08.002