Artículo
Abstract:
With the purpose of synthesizing free 2-thioglycosides of N-acetylneuraminic acid as potential inhibitors of trans-sialidases, a reinvestigation of glycosylation methods was performed. Treatment of methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-α,β-D-glycero-D- galacto-2-nonulopyranosid)oate (1) with thiols in the presence of SnCl4, afforded the β-2-thioglycosides as major products. The methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-3,5-dideoxy-β-D-glycero-D- galacto-2-nonulopyranosid)oate (5) was prepared from 1 with trimethylsilyl bromide. This activated compound led to the 2-thio-α-glycosides when reacted with thiophenols, and to the β anomer by reaction with phenylmethanetiol. These products were characterized as the free ammonium salts. On the other hand, treatment of bromide 5, or the analogue chloride 2, with potassium thiocyanate in acetone led regioselectively to methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-isothiocyano-D-glycero-D- galacto-2-nonulopyranosid)oates, being the β-anomer 13 the major product.
Registro:
| Documento: | Artículo |
| Título: | Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| Autor: | Marino, C.; Varela, O.; De Lederkremer, R.M. |
| Filiación: | CIHIDECAR, Departamento de Química Orgánica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina |
| Año: | 1998 |
| Volumen: | 86 |
| Número: | 3-6 |
| Página de inicio: | 237 |
| Página de fin: | 242 |
| Título revista: | Anales des la Asociacion Quimica Argentina |
| ISSN: | 03650375 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p237_Marino |
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Citas:
---------- APA ----------
Marino, C., Varela, O. & De Lederkremer, R.M. (1998) . Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase. Anales des la Asociacion Quimica Argentina, 86(3-6), 237-242.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p237_Marino [ ]
---------- CHICAGO ----------
Marino, C., Varela, O., De Lederkremer, R.M. "Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase" . Anales des la Asociacion Quimica Argentina 86, no. 3-6 (1998) : 237-242.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p237_Marino [ ]
---------- MLA ----------
Marino, C., Varela, O., De Lederkremer, R.M. "Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase" . Anales des la Asociacion Quimica Argentina, vol. 86, no. 3-6, 1998, pp. 237-242.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p237_Marino [ ]
---------- VANCOUVER ----------
Marino, C., Varela, O., De Lederkremer, R.M. Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase. 1998;86(3-6):237-242.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p237_Marino [ ]
