Comparative Study on the Effects of Picoloyl Groups in Sialylations Based on Their Substitution Pattern
| العنوان: | Comparative Study on the Effects of Picoloyl Groups in Sialylations Based on Their Substitution Pattern |
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| المؤلفون: | Cristina De Meo, Bradley T Jones, Melanie Shadrick, Matthew Lohman, Samira Escopy, Alexanndra Behm, Scott A. Geringer |
| المصدر: | The Journal of Organic Chemistry. 84:15052-15062 |
| بيانات النشر: | American Chemical Society (ACS), 2019. |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | Glycosylation, 010405 organic chemistry, Extramural, Stereochemistry, Hydrogen bond, Organic Chemistry, Hydrogen Bonding, Stereoisomerism, Disaccharides, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, carbohydrates (lipids), chemistry.chemical_compound, chemistry, Carbohydrate Conformation, Sialic Acids, Proton NMR, Glycosyl, Carbohydrate conformation, Triflic acid |
| الوصف: | A novel 8-O-picoloylated sialyl donor has been developed, and the performance of various picoloylated sialyl donors in glycosylations with primary glycosyl acceptors has been evaluated. 8-O-Picoloyl and 4,9-di-O-picoloyl sialyl donors produced moderate to excellent yields of disaccharides with complete α-stereoselectivities. Synergistic effects between picoloyl and the accompanying O-protecting groups (benzoyl vs acetyl) were evaluated, as well as the effects of triflic acid concentration on the 8-O-picoloyl donor. 1H NMR analysis was also carried out to assess differences in the hydrogen-bonding net between sialyl donors. |
| تدمد: | 1520-6904 0022-3263 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a4fa38aebdfea47a9f7fd20c755a14d7Test https://doi.org/10.1021/acs.joc.9b01492Test |
| حقوق: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....a4fa38aebdfea47a9f7fd20c755a14d7 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206904 00223263 |
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