Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation
Conformationally restricted 3,5-O-di-tert-butylsilylene-d-galactofuranosyl trichloroacetimidate donors were synthesized from allyl α-d- galactofuranoside for the construction of 1,2-cis α-d-galactofuranosyl linkages. Glycosylation reactions were performed with several acceptors, including d-galacton...
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2011
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paper:paper_00086215_v346_n18_p2838_Tilve2023-06-08T14:32:59Z Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation 1,2-cis Galactofuranose Glycosylation Protecting groups Solvents effects Trichloroacetimidate 1,2-cis Diethyl ethers Ethereal solvents Galactofuranose Glycosylation reactions Protecting groups Reaction solvents Trichloroacetimidate Esterification Ethers Glycosylation Reaction intermediates Solvents 3,5 o (di tert butylsilylene) dextro galactofuranosyl trichloroacetimidate dextro galactono 1,4 lactone dichloromethane glucose derivative lactone derivative trichloroacetimidic acid unclassified drug article conformation glycosylation priority journal reaction analysis synthesis temperature Carbohydrate Conformation Furans Galactosides Glycosylation Organosilicon Compounds Conformationally restricted 3,5-O-di-tert-butylsilylene-d-galactofuranosyl trichloroacetimidate donors were synthesized from allyl α-d- galactofuranoside for the construction of 1,2-cis α-d-galactofuranosyl linkages. Glycosylation reactions were performed with several acceptors, including d-galactono-1,4-lactone, d-rhamnopyranosyl, and d-mannopyranosyl derivatives. The influence of the temperature and the reaction solvents was evaluated, as well as the 6-O-substitution pattern of the donor. The higher α-selectivities were obtained at -78 °C in diethyl ether as solvent. 6-O-Acetyl substitution on constrained donor increased the α-selectivity compared to the 6-O-benzyl substitution. Almost no selectivities were observed in the non-participating solvent CH 2Cl 2. In contrast, ethereal solvents enhanced the α-selectivity suggesting a participating effect in the reaction intermediate. © 2011 Elsevier Ltd. All rights reserved. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n18_p2838_Tilve http://hdl.handle.net/20.500.12110/paper_00086215_v346_n18_p2838_Tilve |
| 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 Galactofuranose Glycosylation Protecting groups Solvents effects Trichloroacetimidate 1,2-cis Diethyl ethers Ethereal solvents Galactofuranose Glycosylation reactions Protecting groups Reaction solvents Trichloroacetimidate Esterification Ethers Glycosylation Reaction intermediates Solvents 3,5 o (di tert butylsilylene) dextro galactofuranosyl trichloroacetimidate dextro galactono 1,4 lactone dichloromethane glucose derivative lactone derivative trichloroacetimidic acid unclassified drug article conformation glycosylation priority journal reaction analysis synthesis temperature Carbohydrate Conformation Furans Galactosides Glycosylation Organosilicon Compounds |
| spellingShingle |
1,2-cis Galactofuranose Glycosylation Protecting groups Solvents effects Trichloroacetimidate 1,2-cis Diethyl ethers Ethereal solvents Galactofuranose Glycosylation reactions Protecting groups Reaction solvents Trichloroacetimidate Esterification Ethers Glycosylation Reaction intermediates Solvents 3,5 o (di tert butylsilylene) dextro galactofuranosyl trichloroacetimidate dextro galactono 1,4 lactone dichloromethane glucose derivative lactone derivative trichloroacetimidic acid unclassified drug article conformation glycosylation priority journal reaction analysis synthesis temperature Carbohydrate Conformation Furans Galactosides Glycosylation Organosilicon Compounds Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| topic_facet |
1,2-cis Galactofuranose Glycosylation Protecting groups Solvents effects Trichloroacetimidate 1,2-cis Diethyl ethers Ethereal solvents Galactofuranose Glycosylation reactions Protecting groups Reaction solvents Trichloroacetimidate Esterification Ethers Glycosylation Reaction intermediates Solvents 3,5 o (di tert butylsilylene) dextro galactofuranosyl trichloroacetimidate dextro galactono 1,4 lactone dichloromethane glucose derivative lactone derivative trichloroacetimidic acid unclassified drug article conformation glycosylation priority journal reaction analysis synthesis temperature Carbohydrate Conformation Furans Galactosides Glycosylation Organosilicon Compounds |
| description |
Conformationally restricted 3,5-O-di-tert-butylsilylene-d-galactofuranosyl trichloroacetimidate donors were synthesized from allyl α-d- galactofuranoside for the construction of 1,2-cis α-d-galactofuranosyl linkages. Glycosylation reactions were performed with several acceptors, including d-galactono-1,4-lactone, d-rhamnopyranosyl, and d-mannopyranosyl derivatives. The influence of the temperature and the reaction solvents was evaluated, as well as the 6-O-substitution pattern of the donor. The higher α-selectivities were obtained at -78 °C in diethyl ether as solvent. 6-O-Acetyl substitution on constrained donor increased the α-selectivity compared to the 6-O-benzyl substitution. Almost no selectivities were observed in the non-participating solvent CH 2Cl 2. In contrast, ethereal solvents enhanced the α-selectivity suggesting a participating effect in the reaction intermediate. © 2011 Elsevier Ltd. All rights reserved. |
| title |
Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| title_short |
Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| title_full |
Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| title_fullStr |
Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| title_full_unstemmed |
Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| title_sort |
glycosylation studies on conformationally restricted 3,5-o-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation |
| publishDate |
2011 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n18_p2838_Tilve http://hdl.handle.net/20.500.12110/paper_00086215_v346_n18_p2838_Tilve |
| _version_ |
1768545170103468032 |