Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide
The synthesis of crystalline per-0-TBS-β-D-galactofuranose (Aβ) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new e...
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| Formato: | JOUR |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00223263_v74_n5_p1994_Baldoni |
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todo:paper_00223263_v74_n5_p1994_Baldoni2023-10-03T14:31:28Z Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide Baldoni, L. Marino, C. Anomeric Butyldimethylsilyl Facile synthesis Galactofuranose Glycosyl acceptors In-situ Protective groups Simple alcohols Stereoselectivity acetal derivative alcohol derivative furan derivative article glycosylation iodination nuclear magnetic resonance promoter region silylation stereochemistry Carbohydrate Conformation Galactose Glycosylation Hydrocarbons, Iodinated Organosilicon Compounds Stereoisomerism The synthesis of crystalline per-0-TBS-β-D-galactofuranose (Aβ) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high β-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved. © 2009 American Chemical Society. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00223263_v74_n5_p1994_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 |
Anomeric Butyldimethylsilyl Facile synthesis Galactofuranose Glycosyl acceptors In-situ Protective groups Simple alcohols Stereoselectivity acetal derivative alcohol derivative furan derivative article glycosylation iodination nuclear magnetic resonance promoter region silylation stereochemistry Carbohydrate Conformation Galactose Glycosylation Hydrocarbons, Iodinated Organosilicon Compounds Stereoisomerism |
| spellingShingle |
Anomeric Butyldimethylsilyl Facile synthesis Galactofuranose Glycosyl acceptors In-situ Protective groups Simple alcohols Stereoselectivity acetal derivative alcohol derivative furan derivative article glycosylation iodination nuclear magnetic resonance promoter region silylation stereochemistry Carbohydrate Conformation Galactose Glycosylation Hydrocarbons, Iodinated Organosilicon Compounds Stereoisomerism Baldoni, L. Marino, C. Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| topic_facet |
Anomeric Butyldimethylsilyl Facile synthesis Galactofuranose Glycosyl acceptors In-situ Protective groups Simple alcohols Stereoselectivity acetal derivative alcohol derivative furan derivative article glycosylation iodination nuclear magnetic resonance promoter region silylation stereochemistry Carbohydrate Conformation Galactose Glycosylation Hydrocarbons, Iodinated Organosilicon Compounds Stereoisomerism |
| description |
The synthesis of crystalline per-0-TBS-β-D-galactofuranose (Aβ) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high β-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved. © 2009 American Chemical Society. |
| format |
JOUR |
| author |
Baldoni, L. Marino, C. |
| author_facet |
Baldoni, L. Marino, C. |
| author_sort |
Baldoni, L. |
| title |
Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| title_short |
Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| title_full |
Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| title_fullStr |
Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| title_full_unstemmed |
Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| title_sort |
facile synthesis of per-o-tort-butyldimethylsilyl-β-d-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide |
| url |
http://hdl.handle.net/20.500.12110/paper_00223263_v74_n5_p1994_Baldoni |
| work_keys_str_mv |
AT baldonil facilesynthesisofperotortbutyldimethylsilylbdgalactofuranoseandefficientglyeosylationviathegalactofuranosyliodide AT marinoc facilesynthesisofperotortbutyldimethylsilylbdgalactofuranoseandefficientglyeosylationviathegalactofuranosyliodide |
| _version_ |
1782031119236988928 |