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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| Autores principales: | , , |
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| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_15237060_v1_n2_p245_GalloRodriguez |
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| Sumario: | (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. |
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