Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation
Glycosylation studies for the construction of 1,2-cis α-linkages with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including d-mannosyl and l-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH 2Cl2, Et2O,...
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todo:paper_00086215_v346_n12_p1495_Gola2023-10-03T14:07:22Z Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation Gola, G. Tilve, M.J. Gallo-Rodriguez, C. 1,2-Cis Diastereoselectivity Galactofuranose Glycosylation Solvents effects Trichloroacetimidate 1,2-Cis Diastereo-selectivity Galactofuranose Glycosylations Low temperatures Pathogenic microorganisms Pyranose Trichloroacetimidate Acetonitrile Esterification Glycosylation Microorganisms Solvents Thiophene Organic solvents 2 o benzoyl 5,6 o isopropylidene d galactono 1,4 lactone 3,4 di o benzyl alpha rhamnopyranoside acetonitrile lactone methyl 2,3,4 tri o benzoyl alpha d mannopyranoside methyl 2,3,4 tri o benzyl alpha d mannopyranoside methyl 3 o benzoyl 4,6 o benzylidene alpha d mannopyranoside o (2,3,5,6 tetra o benzyl beta d galactofuranosyl)trichloroacetimidate oligosaccharide pyranoside solvent thiophene trichloroacetimidic acid unclassified drug article glycosylation low temperature procedures priority journal synthesis Antigens, Bacterial Antigens, Fungal Bacteria Chromatography, Thin Layer Cold Temperature Fungi Furans Glycoconjugates Glycosylation Magnetic Resonance Spectroscopy Oligosaccharides Solvents Stereoisomerism Trichloroacetic Acid Tetra Glycosylation studies for the construction of 1,2-cis α-linkages with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including d-mannosyl and l-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH 2Cl2, Et2O, and acetonitrile as solvents. A non-participating solvent such as CH2Cl2 at -78 °C, favored the α-d-configuration. In contrast, acetonitrile strongly favored the β-d-configuration, whereas no selectivities were observed with Et 2O. The use of thiophene as an additive did not enhance the α-d-selectivity as in the pyranose counterpart. Although selectivities strongly depended on the acceptor, trichloroacetimidate 1 constitutes a valuable donor for the synthesis of α-d-Galf-(1→2)-l-Rha and α-d-Galf-(1→6)-d-Man. As these motifs are present in pathogenic microorganisms, these procedures described here are useful for the straightforward synthesis of natural oligosaccharides. © 2011 Elsevier Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v346_n12_p1495_Gola |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1,2-Cis Diastereoselectivity Galactofuranose Glycosylation Solvents effects Trichloroacetimidate 1,2-Cis Diastereo-selectivity Galactofuranose Glycosylations Low temperatures Pathogenic microorganisms Pyranose Trichloroacetimidate Acetonitrile Esterification Glycosylation Microorganisms Solvents Thiophene Organic solvents 2 o benzoyl 5,6 o isopropylidene d galactono 1,4 lactone 3,4 di o benzyl alpha rhamnopyranoside acetonitrile lactone methyl 2,3,4 tri o benzoyl alpha d mannopyranoside methyl 2,3,4 tri o benzyl alpha d mannopyranoside methyl 3 o benzoyl 4,6 o benzylidene alpha d mannopyranoside o (2,3,5,6 tetra o benzyl beta d galactofuranosyl)trichloroacetimidate oligosaccharide pyranoside solvent thiophene trichloroacetimidic acid unclassified drug article glycosylation low temperature procedures priority journal synthesis Antigens, Bacterial Antigens, Fungal Bacteria Chromatography, Thin Layer Cold Temperature Fungi Furans Glycoconjugates Glycosylation Magnetic Resonance Spectroscopy Oligosaccharides Solvents Stereoisomerism Trichloroacetic Acid Tetra |
| spellingShingle |
1,2-Cis Diastereoselectivity Galactofuranose Glycosylation Solvents effects Trichloroacetimidate 1,2-Cis Diastereo-selectivity Galactofuranose Glycosylations Low temperatures Pathogenic microorganisms Pyranose Trichloroacetimidate Acetonitrile Esterification Glycosylation Microorganisms Solvents Thiophene Organic solvents 2 o benzoyl 5,6 o isopropylidene d galactono 1,4 lactone 3,4 di o benzyl alpha rhamnopyranoside acetonitrile lactone methyl 2,3,4 tri o benzoyl alpha d mannopyranoside methyl 2,3,4 tri o benzyl alpha d mannopyranoside methyl 3 o benzoyl 4,6 o benzylidene alpha d mannopyranoside o (2,3,5,6 tetra o benzyl beta d galactofuranosyl)trichloroacetimidate oligosaccharide pyranoside solvent thiophene trichloroacetimidic acid unclassified drug article glycosylation low temperature procedures priority journal synthesis Antigens, Bacterial Antigens, Fungal Bacteria Chromatography, Thin Layer Cold Temperature Fungi Furans Glycoconjugates Glycosylation Magnetic Resonance Spectroscopy Oligosaccharides Solvents Stereoisomerism Trichloroacetic Acid Tetra Gola, G. Tilve, M.J. Gallo-Rodriguez, C. Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| topic_facet |
1,2-Cis Diastereoselectivity Galactofuranose Glycosylation Solvents effects Trichloroacetimidate 1,2-Cis Diastereo-selectivity Galactofuranose Glycosylations Low temperatures Pathogenic microorganisms Pyranose Trichloroacetimidate Acetonitrile Esterification Glycosylation Microorganisms Solvents Thiophene Organic solvents 2 o benzoyl 5,6 o isopropylidene d galactono 1,4 lactone 3,4 di o benzyl alpha rhamnopyranoside acetonitrile lactone methyl 2,3,4 tri o benzoyl alpha d mannopyranoside methyl 2,3,4 tri o benzyl alpha d mannopyranoside methyl 3 o benzoyl 4,6 o benzylidene alpha d mannopyranoside o (2,3,5,6 tetra o benzyl beta d galactofuranosyl)trichloroacetimidate oligosaccharide pyranoside solvent thiophene trichloroacetimidic acid unclassified drug article glycosylation low temperature procedures priority journal synthesis Antigens, Bacterial Antigens, Fungal Bacteria Chromatography, Thin Layer Cold Temperature Fungi Furans Glycoconjugates Glycosylation Magnetic Resonance Spectroscopy Oligosaccharides Solvents Stereoisomerism Trichloroacetic Acid Tetra |
| description |
Glycosylation studies for the construction of 1,2-cis α-linkages with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including d-mannosyl and l-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH 2Cl2, Et2O, and acetonitrile as solvents. A non-participating solvent such as CH2Cl2 at -78 °C, favored the α-d-configuration. In contrast, acetonitrile strongly favored the β-d-configuration, whereas no selectivities were observed with Et 2O. The use of thiophene as an additive did not enhance the α-d-selectivity as in the pyranose counterpart. Although selectivities strongly depended on the acceptor, trichloroacetimidate 1 constitutes a valuable donor for the synthesis of α-d-Galf-(1→2)-l-Rha and α-d-Galf-(1→6)-d-Man. As these motifs are present in pathogenic microorganisms, these procedures described here are useful for the straightforward synthesis of natural oligosaccharides. © 2011 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Gola, G. Tilve, M.J. Gallo-Rodriguez, C. |
| author_facet |
Gola, G. Tilve, M.J. Gallo-Rodriguez, C. |
| author_sort |
Gola, G. |
| title |
Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| title_short |
Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| title_full |
Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| title_fullStr |
Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| title_full_unstemmed |
Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| title_sort |
influence of the solvent in low temperature glycosylations with o-(2,3,5,6-tetra-o-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v346_n12_p1495_Gola |
| work_keys_str_mv |
AT golag influenceofthesolventinlowtemperatureglycosylationswitho2356tetraobenzylbdgalactofuranosyltrichloroacetimidatefor12cisadgalactofuranosylation AT tilvemj influenceofthesolventinlowtemperatureglycosylationswitho2356tetraobenzylbdgalactofuranosyltrichloroacetimidatefor12cisadgalactofuranosylation AT gallorodriguezc influenceofthesolventinlowtemperatureglycosylationswitho2356tetraobenzylbdgalactofuranosyltrichloroacetimidatefor12cisadgalactofuranosylation |
| _version_ |
1782027420543483904 |