Synthesis of galactofuranose disaccharides of biological significance
Methyl β-d-galactofuranoside (3) was readily obtained by tin(IV) chloridecatalyzed glycosylation of penta-O-benzoyl-α,β-d-galactofuranose (1), followed by debenzoylation with sodium methoxide. Glycosylation of 1 with 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (4) or with the 6-O-trityl-lactone deri...
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todo:paper_00086215_v190_n1_p65_Marino2023-10-03T14:06:30Z Synthesis of galactofuranose disaccharides of biological significance Marino, C. Varela, O. de Lederkremer, R.M. disaccharide galactose galactoside glycoside article chemical structure chemistry comparative study conformation glycosylation Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides nuclear magnetic resonance spectroscopy oxidation reduction reaction synthesis Carbohydrate Conformation Chemistry Comparative Study Disaccharides Galactose Galactosides Glycosides Glycosylation Magnetic Resonance Spectroscopy Molecular Structure Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides Oxidation-Reduction Support, Non-U.S. Gov't Methyl β-d-galactofuranoside (3) was readily obtained by tin(IV) chloridecatalyzed glycosylation of penta-O-benzoyl-α,β-d-galactofuranose (1), followed by debenzoylation with sodium methoxide. Glycosylation of 1 with 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (4) or with the 6-O-trityl-lactone derivative 5 gave the benzoylated β-d-galactofuranosyl-(1→6)-d-galactono-1,4-lactone 6 in excellent yield. The structure of disaccharide 6 was confirmed by borohydride reduction to the glycosyl-alditol 7. A byproduct of the condensation reaction of 1 with 4 or 5 was identified as the benzoylated (1→1)-β,β′-d-galactofuranosyl disaccharide 8. Compound 8 was readily prepared (88% yield) by controlled addition of water to 1, in the presence of stannic chloride. O-Debenzoylation of 8 afforded crystalline β′-d-galactofuranosyl-(1→1)-β-d-galactofuranoside (9). The glycosyl-lactone 6 constitutes a key intermediate for the synthesis of a disaccharide derivative having both units in the furanoid form. Thus, diisoamylborane reduction of the lactone function of 6 led to the disaccharide derivative 10, from which the methyl glycoside 12 was prepared. O-Debenzoylation of 12 gave the corresponding methyl β-d-galactofuranosyl-(1→6)-β-d-galactofuranoside (13). The free disaccharide β-d-Galf-(1→6)-d-Galp (14) and its acetylated derivative (15) were also synthesized from 10. © 1989. 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. 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_v190_n1_p65_Marino |
| 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 galactose galactoside glycoside article chemical structure chemistry comparative study conformation glycosylation Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides nuclear magnetic resonance spectroscopy oxidation reduction reaction synthesis Carbohydrate Conformation Chemistry Comparative Study Disaccharides Galactose Galactosides Glycosides Glycosylation Magnetic Resonance Spectroscopy Molecular Structure Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides Oxidation-Reduction Support, Non-U.S. Gov't |
| spellingShingle |
disaccharide galactose galactoside glycoside article chemical structure chemistry comparative study conformation glycosylation Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides nuclear magnetic resonance spectroscopy oxidation reduction reaction synthesis Carbohydrate Conformation Chemistry Comparative Study Disaccharides Galactose Galactosides Glycosides Glycosylation Magnetic Resonance Spectroscopy Molecular Structure Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides Oxidation-Reduction Support, Non-U.S. Gov't Marino, C. Varela, O. de Lederkremer, R.M. Synthesis of galactofuranose disaccharides of biological significance |
| topic_facet |
disaccharide galactose galactoside glycoside article chemical structure chemistry comparative study conformation glycosylation Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides nuclear magnetic resonance spectroscopy oxidation reduction reaction synthesis Carbohydrate Conformation Chemistry Comparative Study Disaccharides Galactose Galactosides Glycosides Glycosylation Magnetic Resonance Spectroscopy Molecular Structure Mycobacterium leprae Mycobacterium tuberculosis Mycoplasma mycoides Oxidation-Reduction Support, Non-U.S. Gov't |
| description |
Methyl β-d-galactofuranoside (3) was readily obtained by tin(IV) chloridecatalyzed glycosylation of penta-O-benzoyl-α,β-d-galactofuranose (1), followed by debenzoylation with sodium methoxide. Glycosylation of 1 with 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (4) or with the 6-O-trityl-lactone derivative 5 gave the benzoylated β-d-galactofuranosyl-(1→6)-d-galactono-1,4-lactone 6 in excellent yield. The structure of disaccharide 6 was confirmed by borohydride reduction to the glycosyl-alditol 7. A byproduct of the condensation reaction of 1 with 4 or 5 was identified as the benzoylated (1→1)-β,β′-d-galactofuranosyl disaccharide 8. Compound 8 was readily prepared (88% yield) by controlled addition of water to 1, in the presence of stannic chloride. O-Debenzoylation of 8 afforded crystalline β′-d-galactofuranosyl-(1→1)-β-d-galactofuranoside (9). The glycosyl-lactone 6 constitutes a key intermediate for the synthesis of a disaccharide derivative having both units in the furanoid form. Thus, diisoamylborane reduction of the lactone function of 6 led to the disaccharide derivative 10, from which the methyl glycoside 12 was prepared. O-Debenzoylation of 12 gave the corresponding methyl β-d-galactofuranosyl-(1→6)-β-d-galactofuranoside (13). The free disaccharide β-d-Galf-(1→6)-d-Galp (14) and its acetylated derivative (15) were also synthesized from 10. © 1989. |
| format |
JOUR |
| author |
Marino, C. Varela, O. de Lederkremer, R.M. |
| author_facet |
Marino, C. Varela, O. de Lederkremer, R.M. |
| author_sort |
Marino, C. |
| title |
Synthesis of galactofuranose disaccharides of biological significance |
| title_short |
Synthesis of galactofuranose disaccharides of biological significance |
| title_full |
Synthesis of galactofuranose disaccharides of biological significance |
| title_fullStr |
Synthesis of galactofuranose disaccharides of biological significance |
| title_full_unstemmed |
Synthesis of galactofuranose disaccharides of biological significance |
| title_sort |
synthesis of galactofuranose disaccharides of biological significance |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v190_n1_p65_Marino |
| work_keys_str_mv |
AT marinoc synthesisofgalactofuranosedisaccharidesofbiologicalsignificance AT varelao synthesisofgalactofuranosedisaccharidesofbiologicalsignificance AT delederkremerrm synthesisofgalactofuranosedisaccharidesofbiologicalsignificance |
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1782027270762790912 |