Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose
Benzoylation of d-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23°, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-d-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-g...
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1990
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v200_nC_p227_deLederkremer http://hdl.handle.net/20.500.12110/paper_00086215_v200_nC_p227_deLederkremer |
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paper:paper_00086215_v200_nC_p227_deLederkremer2023-06-08T14:32:25Z Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose Muchnik de Lederkremer, Rosa María Marino, María Carla Varela, Oscar José 3,5 di O (beta galactofuranosyl) galactofuranose 3,5-di-O-(beta-galactofuranosyl)-galactofuranose 5 O beta galactofuranosyl galactofuranose 5-O-beta-galactofuranosyl-galactofuranose disaccharide trisaccharide article carbohydrate analysis chemistry molecular genetics synthesis Carbohydrate Sequence Chemistry Disaccharides Molecular Sequence Data Support, Non-U.S. Gov't Trisaccharides Benzoylation of d-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23°, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-d-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (4, 70%), HO-3 of which was benzoylated to give 5. The structure of 4 was confirmed by its conversion into crystalline β-d-Galf-(1→5)-d-Gal-ol (8). Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave β-d-Galf-(1→5)-d-Galf (7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (9), which was converted, as for 5, into β-d-Galf-(1→3)[β-d-Galf-(1→5)]-d-Galf (13). © 1990. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Marino, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1990 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v200_nC_p227_deLederkremer http://hdl.handle.net/20.500.12110/paper_00086215_v200_nC_p227_deLederkremer |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
3,5 di O (beta galactofuranosyl) galactofuranose 3,5-di-O-(beta-galactofuranosyl)-galactofuranose 5 O beta galactofuranosyl galactofuranose 5-O-beta-galactofuranosyl-galactofuranose disaccharide trisaccharide article carbohydrate analysis chemistry molecular genetics synthesis Carbohydrate Sequence Chemistry Disaccharides Molecular Sequence Data Support, Non-U.S. Gov't Trisaccharides |
| spellingShingle |
3,5 di O (beta galactofuranosyl) galactofuranose 3,5-di-O-(beta-galactofuranosyl)-galactofuranose 5 O beta galactofuranosyl galactofuranose 5-O-beta-galactofuranosyl-galactofuranose disaccharide trisaccharide article carbohydrate analysis chemistry molecular genetics synthesis Carbohydrate Sequence Chemistry Disaccharides Molecular Sequence Data Support, Non-U.S. Gov't Trisaccharides Muchnik de Lederkremer, Rosa María Marino, María Carla Varela, Oscar José Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| topic_facet |
3,5 di O (beta galactofuranosyl) galactofuranose 3,5-di-O-(beta-galactofuranosyl)-galactofuranose 5 O beta galactofuranosyl galactofuranose 5-O-beta-galactofuranosyl-galactofuranose disaccharide trisaccharide article carbohydrate analysis chemistry molecular genetics synthesis Carbohydrate Sequence Chemistry Disaccharides Molecular Sequence Data Support, Non-U.S. Gov't Trisaccharides |
| description |
Benzoylation of d-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23°, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-d-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (4, 70%), HO-3 of which was benzoylated to give 5. The structure of 4 was confirmed by its conversion into crystalline β-d-Galf-(1→5)-d-Gal-ol (8). Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave β-d-Galf-(1→5)-d-Galf (7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (9), which was converted, as for 5, into β-d-Galf-(1→3)[β-d-Galf-(1→5)]-d-Galf (13). © 1990. |
| author |
Muchnik de Lederkremer, Rosa María Marino, María Carla Varela, Oscar José |
| author_facet |
Muchnik de Lederkremer, Rosa María Marino, María Carla Varela, Oscar José |
| author_sort |
Muchnik de Lederkremer, Rosa María |
| title |
Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| title_short |
Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| title_full |
Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| title_fullStr |
Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| title_full_unstemmed |
Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| title_sort |
convenient syntheses of 5-o- and 3,5-di-o-(β-d-galactofuranosyl)-d-galactofuranose |
| publishDate |
1990 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v200_nC_p227_deLederkremer http://hdl.handle.net/20.500.12110/paper_00086215_v200_nC_p227_deLederkremer |
| work_keys_str_mv |
AT muchnikdelederkremerrosamaria convenientsynthesesof5oand35diobdgalactofuranosyldgalactofuranose AT marinomariacarla convenientsynthesesof5oand35diobdgalactofuranosyldgalactofuranose AT varelaoscarjose convenientsynthesesof5oand35diobdgalactofuranosyldgalactofuranose |
| _version_ |
1768545674947723264 |