A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit
The lactonic disaccharide 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-d-galactono-1,4-lactone (7) was prepared by condensing 6-O-trityl-2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (2) with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (4) or with 1,2,3,4,6-penta-O-acetyl-...
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todo:paper_00086215_v189_nC_p79_duMortier2023-10-03T14:06:30Z A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit du Mortier, C. Varela, O. de Lederkremer, R.M. The lactonic disaccharide 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-d-galactono-1,4-lactone (7) was prepared by condensing 6-O-trityl-2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (2) with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (4) or with 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose (6). The reaction was carried out using various catalysts. In the presence of silver trifluoromethanesulfonate or tin(IV) chloride, formation of the 1,2-trans glycosidic bond took place stereoselectively, to afford compound 7 in good yields. However, condensation of 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (3) with 4 catalyzed by mercuric salts gave 3,4,6-tri-O-acetyl-1,2-O-[1(S)-(2,3,5-tri-O-benzoyl-d-galactono-1,4-lacton-6-yloxy)ethylidene]-α-d- glucopyranose (5) as the main product. Reduction of the lactone function of 7 with bis(3-methyl-2-butyl)borane led to 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-β-d-galactofuranose (8). © 1989. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v189_nC_p79_duMortier |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
The lactonic disaccharide 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-d-galactono-1,4-lactone (7) was prepared by condensing 6-O-trityl-2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (2) with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (4) or with 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose (6). The reaction was carried out using various catalysts. In the presence of silver trifluoromethanesulfonate or tin(IV) chloride, formation of the 1,2-trans glycosidic bond took place stereoselectively, to afford compound 7 in good yields. However, condensation of 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (3) with 4 catalyzed by mercuric salts gave 3,4,6-tri-O-acetyl-1,2-O-[1(S)-(2,3,5-tri-O-benzoyl-d-galactono-1,4-lacton-6-yloxy)ethylidene]-α-d- glucopyranose (5) as the main product. Reduction of the lactone function of 7 with bis(3-methyl-2-butyl)borane led to 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-β-d-galactofuranose (8). © 1989. |
| format |
JOUR |
| author |
du Mortier, C. Varela, O. de Lederkremer, R.M. |
| spellingShingle |
du Mortier, C. Varela, O. de Lederkremer, R.M. A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| author_facet |
du Mortier, C. Varela, O. de Lederkremer, R.M. |
| author_sort |
du Mortier, C. |
| title |
A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| title_short |
A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| title_full |
A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| title_fullStr |
A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| title_full_unstemmed |
A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| title_sort |
new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v189_nC_p79_duMortier |
| work_keys_str_mv |
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| _version_ |
1807318309816762368 |