Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor
The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C- and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v362_n_p70_Baldoni |
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todo:paper_00086215_v362_n_p70_Baldoni2023-10-03T14:07:30Z Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor Baldoni, L. Marino, C. C-Galactofuranosylation Galactofuranosyl iodide Per-tert-butyldimethylsilyl-β-d-galactofuranose S-Galactofuranosylation Alternative approach Anomerics C-Galactofuranosylation Galactofuranosyl iodide Glycomimetics Glycosyl donors S-Galactofuranosylation Organic compounds Synthesis (chemical) Chemical compounds 1 galactofuranosylthiol derivative furan derivative galactofuranoside galactofuranosyl iodide iodide nucleophile thiol derivative unclassified drug article carbohydrate synthesis chemical reaction galactofuranosylation glycosylation iodination priority journal synthesis Galactosides Glycosylation Halogenation Magnetic Resonance Spectroscopy Stereoisomerism Sulfhydryl Compounds Trimethylsilyl Compounds The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C- and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with value as glycomimetics or as precursors of glycobiological tools were synthesized. Among them, the synthesis of the isolable 1-galactofuranosylthiol 15 is remarkable, as it paves the way for alternative approaches for S-galactofuranosyl derivatives. © 2012 Elsevier Ltd. All rights reserved. Fil:Baldoni, L. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v362_n_p70_Baldoni |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
C-Galactofuranosylation Galactofuranosyl iodide Per-tert-butyldimethylsilyl-β-d-galactofuranose S-Galactofuranosylation Alternative approach Anomerics C-Galactofuranosylation Galactofuranosyl iodide Glycomimetics Glycosyl donors S-Galactofuranosylation Organic compounds Synthesis (chemical) Chemical compounds 1 galactofuranosylthiol derivative furan derivative galactofuranoside galactofuranosyl iodide iodide nucleophile thiol derivative unclassified drug article carbohydrate synthesis chemical reaction galactofuranosylation glycosylation iodination priority journal synthesis Galactosides Glycosylation Halogenation Magnetic Resonance Spectroscopy Stereoisomerism Sulfhydryl Compounds Trimethylsilyl Compounds |
| spellingShingle |
C-Galactofuranosylation Galactofuranosyl iodide Per-tert-butyldimethylsilyl-β-d-galactofuranose S-Galactofuranosylation Alternative approach Anomerics C-Galactofuranosylation Galactofuranosyl iodide Glycomimetics Glycosyl donors S-Galactofuranosylation Organic compounds Synthesis (chemical) Chemical compounds 1 galactofuranosylthiol derivative furan derivative galactofuranoside galactofuranosyl iodide iodide nucleophile thiol derivative unclassified drug article carbohydrate synthesis chemical reaction galactofuranosylation glycosylation iodination priority journal synthesis Galactosides Glycosylation Halogenation Magnetic Resonance Spectroscopy Stereoisomerism Sulfhydryl Compounds Trimethylsilyl Compounds Baldoni, L. Marino, C. Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| topic_facet |
C-Galactofuranosylation Galactofuranosyl iodide Per-tert-butyldimethylsilyl-β-d-galactofuranose S-Galactofuranosylation Alternative approach Anomerics C-Galactofuranosylation Galactofuranosyl iodide Glycomimetics Glycosyl donors S-Galactofuranosylation Organic compounds Synthesis (chemical) Chemical compounds 1 galactofuranosylthiol derivative furan derivative galactofuranoside galactofuranosyl iodide iodide nucleophile thiol derivative unclassified drug article carbohydrate synthesis chemical reaction galactofuranosylation glycosylation iodination priority journal synthesis Galactosides Glycosylation Halogenation Magnetic Resonance Spectroscopy Stereoisomerism Sulfhydryl Compounds Trimethylsilyl Compounds |
| description |
The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C- and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with value as glycomimetics or as precursors of glycobiological tools were synthesized. Among them, the synthesis of the isolable 1-galactofuranosylthiol 15 is remarkable, as it paves the way for alternative approaches for S-galactofuranosyl derivatives. © 2012 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Baldoni, L. Marino, C. |
| author_facet |
Baldoni, L. Marino, C. |
| author_sort |
Baldoni, L. |
| title |
Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| title_short |
Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| title_full |
Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| title_fullStr |
Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| title_full_unstemmed |
Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| title_sort |
synthesis of s- and c-galactofuranosides via a galactofuranosyl iodide. isolable 1-galactofuranosylthiol derivative as a new glycosyl donor |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v362_n_p70_Baldoni |
| work_keys_str_mv |
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| _version_ |
1807321845664317440 |