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Gallo-Rodriguez, C.; Kashiwagi, G.A. "Selective Glycosylations with Furanosides" (2017) Selective Glycosylation: Synthetic Methods and Catalysts:297-326
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Abstract:

This chapter focuses on recent advances in the furanose glycosylation field, including its scope and limitations. The findings in the furanose glycosylation field usually follow the findings on pyranose compounds. The reactivities of pyranoses and furanoses are quite different. The approaches developed to access to furanosyl templates include the following: kinetically controlled Fisher glycosylation, dithioacetal cyclization, high-temperature acylation, glycal ozonolysis, aldonolactone reduction, formation of borate complexes, and formation of 1,4-anhydrosugars. The selection of the furanosyl template is in close relationship with the glycosylation method chosen. The next step involves the stereoselective control of the furanosylation reaction. A similar study was performed on stereochemically related D-galactofuranosyl thioglycoside donors carrying several silyl, benzoyl, and 3,5-O-di-tertbutylsilylene- protecting groups. Partially protected thiogalactofuranoside and thioarabinofuranoside donors were used as key glycosylating building blocks in one-pot syntheses of several oligosaccharides constituents of pathogenic microorganisms. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA.

Registro:

Documento: Parte de libro
Título:Selective Glycosylations with Furanosides
Autor:Gallo-Rodriguez, C.; Kashiwagi, G.A.
Filiación:Universidad de Buenos Aires, CIHIDECAR Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, Buenos Aires, 1428, Argentina
Palabras clave:Fisher glycosylation; Furanose glycosylation field; Furanose template; Furanosylation reaction; Oligosaccharide synthesis; Pyranose compounds; Stereoselective glycosylation; Thioarabinofuranoside donor; Thiogalactofuranoside donor; Microorganisms; Oligosaccharides; Ozone; Stereoselectivity; Furanose; Furanosylation reaction; Oligosaccharide synthesis; Pyranose; Stereo-selective; Thioarabinofuranoside donor; Thiogalactofuranoside donor; Glycosylation
Año:2017
Página de inicio:297
Página de fin:326
DOI: http://dx.doi.org/10.1002/9783527696239.ch14
Título revista:Selective Glycosylation: Synthetic Methods and Catalysts
Título revista abreviado:Sel. Glycosylation: Synth. Method. and Catal.
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_97835276_v_n_p297_GalloRodriguez

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Citas:

---------- APA ----------
Gallo-Rodriguez, C. & Kashiwagi, G.A. (2017) . Selective Glycosylations with Furanosides. Selective Glycosylation: Synthetic Methods and Catalysts, 297-326.
http://dx.doi.org/10.1002/9783527696239.ch14
---------- CHICAGO ----------
Gallo-Rodriguez, C., Kashiwagi, G.A. "Selective Glycosylations with Furanosides" . Selective Glycosylation: Synthetic Methods and Catalysts (2017) : 297-326.
http://dx.doi.org/10.1002/9783527696239.ch14
---------- MLA ----------
Gallo-Rodriguez, C., Kashiwagi, G.A. "Selective Glycosylations with Furanosides" . Selective Glycosylation: Synthetic Methods and Catalysts, 2017, pp. 297-326.
http://dx.doi.org/10.1002/9783527696239.ch14
---------- VANCOUVER ----------
Gallo-Rodriguez, C., Kashiwagi, G.A. Selective Glycosylations with Furanosides. Sel. Glycosylation: Synth. Method. and Catal. 2017:297-326.
http://dx.doi.org/10.1002/9783527696239.ch14