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Abstract:

Michael addition of 1,2:3,4-di-O-isopropylidene-6-thio-α-d-galactose (2) to 2-propyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3-enopyranosid-2-ulose (1) afforded, as the major diastereoisomer, 2-propyl 6-O-acetyl-3-deoxy-4-S-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-ga lactopyranos-6-yl)-4-thio-α-d-threo-hexopyranosid-2-ulose (3, 91% yield). Reduction of the carbonyl group of 3, followed by O-deacetylation gave the two epimers 7 (α-d-lyxo) and 8 (α-d-xylo) in a 1:2 ratio. On removal of the protecting groups of 8 by acid hydrolysis, formation of an 1,6-anhydro bridge was observed in the 3-deoxy-4-thiohexopyranose unit (10). The free non-glycosidic thioether-linked disaccharide 3-deoxy-4-S-(6-deoxy-α,β-d-galactopyranos-6-yl)-4-thio- α,β-d-xylo-hexopyranose (11) was obtained by acetolysis of 10 followed by O-deacetylation. A similar sequence starting from the enone 1 and methyl 2,3,4-tri-O-benzoyl-6-thio-α-d-glucopyranoside (12) led successfully to 2-propyl 3-deoxy-4-S-(methyl 6-deoxy-α-d-glucopyranos-6-yl)-4-thio-α-d-lyxo-hexopyranosid e (17) and its α-d-xylo analog (19, major product). In this synthetic route, orthogonal sets of protecting groups were employed to preserve the configuration of both reducing ends and to avoid the formation of the 1,6-anhydro ring. © 2007 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics
Autor:Uhrig, M.L.; Szilágyi, L.; Kövér, K.E.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Department of Organic Chemistry, University of Debrecen, pf. 20, H-4010 Debrecen, Hungary
Department of Inorganic Chemistry, University of Debrecen, pf. 20, H-4010 Debrecen, Hungary
Palabras clave:4,6′-Thioether-linked sugars; Michael addition; Sugar enones; Thioether-linked disaccharide analogues; Acid hydrolysis; Diastereoisomer; Disaccharides; Glycomimetics; Michael addition; Acetylation; Addition reactions; Chemical bonds; Chemical stability; Hydrolysis; Synthesis (chemical); Sugars; 2 propyl 3 deoxy 4 s (methyl 6 deoxy alpha dextro glucopyranos 6 yl) 4 thio alpha dextro xylo hexopyranoside; 3 deoxy 4 thiohexopyranose; carbonyl derivative; disaccharide; methyl 2,3,4 tri o benzoyl 6 thio alpha dextro glycopyranoside; pyran derivative; pyranoside; unclassified drug; article; chemical modification; deacetylation; hydrolysis; Michael addition; priority journal; stereochemistry; synthesis; Carbohydrate Conformation; Disaccharides; Glycosides; Hypoglycemic Agents; Models, Molecular; Sulfides
Año:2007
Volumen:342
Número:12-13
Página de inicio:1841
Página de fin:1849
DOI: http://dx.doi.org/10.1016/j.carres.2007.03.025
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:Disaccharides; Glycosides; Hypoglycemic Agents; Sulfides; coyolosa
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v342_n12-13_p1841_Uhrig

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Citas:

---------- APA ----------
Uhrig, M.L., Szilágyi, L., Kövér, K.E. & Varela, O. (2007) . Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics. Carbohydrate Research, 342(12-13), 1841-1849.
http://dx.doi.org/10.1016/j.carres.2007.03.025
---------- CHICAGO ----------
Uhrig, M.L., Szilágyi, L., Kövér, K.E., Varela, O. "Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics" . Carbohydrate Research 342, no. 12-13 (2007) : 1841-1849.
http://dx.doi.org/10.1016/j.carres.2007.03.025
---------- MLA ----------
Uhrig, M.L., Szilágyi, L., Kövér, K.E., Varela, O. "Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics" . Carbohydrate Research, vol. 342, no. 12-13, 2007, pp. 1841-1849.
http://dx.doi.org/10.1016/j.carres.2007.03.025
---------- VANCOUVER ----------
Uhrig, M.L., Szilágyi, L., Kövér, K.E., Varela, O. Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics. Carbohydr. Res. 2007;342(12-13):1841-1849.
http://dx.doi.org/10.1016/j.carres.2007.03.025