Photo Amidoglycosylation of an Allal Azidoformate. Synthesis of β-2-Amido Allopyranosides
| Autor: | Cindy Kan, Charli M. Long, Sarah E. Tully, Moushumi Paul, Christian M. Rojas, Christina M. Ring |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Azides Glycosylation Photolysis Formates Glycal Dibutyltin oxide Nitrene Organic Chemistry Alcohol Amides Biochemistry chemistry.chemical_compound Hydrolysis chemistry Nucleophile Intramolecular force Trimethylsilyl azide Carbohydrate Conformation Organic chemistry Glycosides Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 3:381-384 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol0069002 |
| Popis: | [figure: see text] Photolysis of an allal C-3 azidoformate provoked intramolecular nitrene insertion into the glycal C=C unit and allowed direct incorporation of alcohol nucleophiles as beta-disposed substituents at C-1. The 2-amido allopyranoside products were elaborated via N-acylation and selective oxazolidinone hydrolysis, providing N-Boc-protected 2-amino sugars and simplifying stereochemical assignments. Synthesis of the potentially labile allal azidoformate was achieved via reaction of the corresponding carbonyl imidazolide with trimethylsilyl azide, facilitated by dibutyltin oxide. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|