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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Autores principales:	de Lederkremer, R.M., Marino, C., Varela, O.
Formato:	JOUR
Materias:	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
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_00086215_v200_nC_p227_deLederkremer
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_00086215_v200_nC_p227_deLederkremer2023-10-03T14:06:33Z Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose de Lederkremer, R.M. Marino, C. Varela, O. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 de Lederkremer, R.M. Marino, C. Varela, O. 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.
format	JOUR
author	de Lederkremer, R.M. Marino, C. Varela, O.
author_facet	de Lederkremer, R.M. Marino, C. Varela, O.
author_sort	de Lederkremer, R.M.
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
url	http://hdl.handle.net/20.500.12110/paper_00086215_v200_nC_p227_deLederkremer
work_keys_str_mv	AT delederkremerrm convenientsynthesesof5oand35diobdgalactofuranosyldgalactofuranose AT marinoc convenientsynthesesof5oand35diobdgalactofuranosyldgalactofuranose AT varelao convenientsynthesesof5oand35diobdgalactofuranosyldgalactofuranose
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Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose

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