Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate
Per-O-tert-butyldimethylsilyl-α,β-d-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-β-d- galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-α-d-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate wa...
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todo:paper_00086215_v346_n2_p191_Baldoni2023-10-03T14:07:23Z Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate Baldoni, L. Stortz, C.A. Marino, C. Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Glycosylation Molecular modeling Sugar (sucrose) Synthesis (chemical) Conformations 1,2 cis fused bicyclic alpha galactofuranosyl thiocarbamic acid isothiocyanic acid derivative per o tert butyldimethylsilyl beta galactofuranosyl isothiocyanic acid thiocarbamic acid derivative thiocyanate potassium unclassified drug article conformation controlled study molecular model priority journal proton nuclear magnetic resonance silylation synthesis Galactose Isothiocyanates Models, Molecular Molecular Conformation Organosilicon Compounds Oxazoles Thiocarbamates Per-O-tert-butyldimethylsilyl-α,β-d-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-β-d- galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-α-d-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (3T4 and 4TO) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents. © 2010 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_n2_p191_Baldoni |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Glycosylation Molecular modeling Sugar (sucrose) Synthesis (chemical) Conformations 1,2 cis fused bicyclic alpha galactofuranosyl thiocarbamic acid isothiocyanic acid derivative per o tert butyldimethylsilyl beta galactofuranosyl isothiocyanic acid thiocarbamic acid derivative thiocyanate potassium unclassified drug article conformation controlled study molecular model priority journal proton nuclear magnetic resonance silylation synthesis Galactose Isothiocyanates Models, Molecular Molecular Conformation Organosilicon Compounds Oxazoles Thiocarbamates |
| spellingShingle |
Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Glycosylation Molecular modeling Sugar (sucrose) Synthesis (chemical) Conformations 1,2 cis fused bicyclic alpha galactofuranosyl thiocarbamic acid isothiocyanic acid derivative per o tert butyldimethylsilyl beta galactofuranosyl isothiocyanic acid thiocarbamic acid derivative thiocyanate potassium unclassified drug article conformation controlled study molecular model priority journal proton nuclear magnetic resonance silylation synthesis Galactose Isothiocyanates Models, Molecular Molecular Conformation Organosilicon Compounds Oxazoles Thiocarbamates Baldoni, L. Stortz, C.A. Marino, C. Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| topic_facet |
Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Conformational analysis Cyclic thiocarbamate Galactofuranosyl isothiocyanate Glycosyl iodide Molecular modelling Glycosylation Molecular modeling Sugar (sucrose) Synthesis (chemical) Conformations 1,2 cis fused bicyclic alpha galactofuranosyl thiocarbamic acid isothiocyanic acid derivative per o tert butyldimethylsilyl beta galactofuranosyl isothiocyanic acid thiocarbamic acid derivative thiocyanate potassium unclassified drug article conformation controlled study molecular model priority journal proton nuclear magnetic resonance silylation synthesis Galactose Isothiocyanates Models, Molecular Molecular Conformation Organosilicon Compounds Oxazoles Thiocarbamates |
| description |
Per-O-tert-butyldimethylsilyl-α,β-d-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-β-d- galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-α-d-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (3T4 and 4TO) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents. © 2010 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Baldoni, L. Stortz, C.A. Marino, C. |
| author_facet |
Baldoni, L. Stortz, C.A. Marino, C. |
| author_sort |
Baldoni, L. |
| title |
Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| title_short |
Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| title_full |
Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| title_fullStr |
Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| title_full_unstemmed |
Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| title_sort |
synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-o-tert-butyldimethylsilyl- β-d-galactofuranosyl isothiocyanate |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v346_n2_p191_Baldoni |
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| _version_ |
1782024007520878592 |