Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation
(equation presented) In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. β-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step. The mild conditions...
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1999
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez http://hdl.handle.net/20.500.12110/paper_15237060_v1_n2_p245_GalloRodriguez |
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paper:paper_15237060_v1_n2_p245_GalloRodriguez2023-06-08T16:19:27Z Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation disaccharide galactofuranosyl 1 3 N acetylglucosamine galactofuranosyl 1 6 N acetylglucosamine galactofuranosyl-1-3-N-acetylglucosamine galactofuranosyl-1-6-N-acetylglucosamine mucin stannic chloride tin derivative animal article catalysis chemistry glycosylation synthesis Trypanosoma cruzi Animals Catalysis Disaccharides Glycosylation Mucins Tin Compounds Trypanosoma cruzi (equation presented) In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. β-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step. The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside (11) with penta-O-benzoyl-α,β-D-galactofuranose (4) gave the derivative of β-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield. 1999 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez http://hdl.handle.net/20.500.12110/paper_15237060_v1_n2_p245_GalloRodriguez |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
disaccharide galactofuranosyl 1 3 N acetylglucosamine galactofuranosyl 1 6 N acetylglucosamine galactofuranosyl-1-3-N-acetylglucosamine galactofuranosyl-1-6-N-acetylglucosamine mucin stannic chloride tin derivative animal article catalysis chemistry glycosylation synthesis Trypanosoma cruzi Animals Catalysis Disaccharides Glycosylation Mucins Tin Compounds Trypanosoma cruzi |
| spellingShingle |
disaccharide galactofuranosyl 1 3 N acetylglucosamine galactofuranosyl 1 6 N acetylglucosamine galactofuranosyl-1-3-N-acetylglucosamine galactofuranosyl-1-6-N-acetylglucosamine mucin stannic chloride tin derivative animal article catalysis chemistry glycosylation synthesis Trypanosoma cruzi Animals Catalysis Disaccharides Glycosylation Mucins Tin Compounds Trypanosoma cruzi Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| topic_facet |
disaccharide galactofuranosyl 1 3 N acetylglucosamine galactofuranosyl 1 6 N acetylglucosamine galactofuranosyl-1-3-N-acetylglucosamine galactofuranosyl-1-6-N-acetylglucosamine mucin stannic chloride tin derivative animal article catalysis chemistry glycosylation synthesis Trypanosoma cruzi Animals Catalysis Disaccharides Glycosylation Mucins Tin Compounds Trypanosoma cruzi |
| description |
(equation presented) In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. β-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step. The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside (11) with penta-O-benzoyl-α,β-D-galactofuranose (4) gave the derivative of β-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield. |
| title |
Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| title_short |
Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| title_full |
Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| title_fullStr |
Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| title_full_unstemmed |
Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| title_sort |
synthesis of β-d-galf-(1-3)-d-glcnac by the trichloroacetamidate method and of β-d-galf-(1-6)-d-glcnac by sncl4-promoted glycosylation |
| publishDate |
1999 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez http://hdl.handle.net/20.500.12110/paper_15237060_v1_n2_p245_GalloRodriguez |
| _version_ |
1768545895774683136 |