Catalytic Site-Selective Carbamoylation of Pyranosides
| Autor: | Lucas Petitpoisson, André Pichette, Jérôme Alsarraf |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Organic Chemistry Glycoside 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Reagent Site selective Moiety Physical and Theoretical Chemistry Phosgene Borinic acid |
| Zdroj: | Organic Letters. 23:6052-6056 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Carbamate-bearing carbohydrates contribute to the pharmacological properties of various natural glycosides. The catalytic site-selective carbamoylation of minimally protected pyranosides was achieved for the first time to bypass protection/deprotection sequences. 1-Carbamoylimidazoles were used as the carbamoylation reagents to circumvent the harmful and unstable phosgene and isocyanates. This borinic acid catalyzed transformation granted an expedient access to the tumor cell-binding carbamoylmannoside moiety of bleomycins and analogs in yields of 56% to 89%. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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