On the Use of (4S,5S)-2-Phenyl-4,5-Dimethyl-4-Formyl-4,5-Dihydro-Oxazole in the Synthesis of N-Protected 2,3,4,6-Tetradeoxy-4-C-Methyl-4-Amino-L-Hexose Derivatives

Autor:	Claudio Fuganti, Giovanni Fronza, Andrea Mele, G. Pedrocchi Fantoni
Rok vydání:	1991
Předmět:	chemistry.chemical_classification Anomer Stereochemistry Organic Chemistry chemistry.chemical_element Biochemistry Sulfur Aldehyde Adduct chemistry.chemical_compound chemistry Nucleophile Proton NMR Hexose Oxazole
Zdroj:	Journal of Carbohydrate Chemistry. 10:197-213
ISSN:	1532-2327 0732-8303
DOI:	10.1080/07328309108543901
Popis:	The (4S,5S)-2-phenyl-4,5-dimethyl-4-formyl-4,5-dihydro-oxazole (4), via the α, β-unsaturated ester 5 and re-face addition of nitrogen and sulfur nucleophiles, gave eventually the ribo-imidazolino hexose 15 and the methyl α and β-2,3,4-6-tetradeoxy-4-C-methyl-4-trifluoroacetamido-3-thia-L-ribo-hexopyranoside (16). Addition via the adduct 17 afforded the arabino-3,4-diamino derivative 20 and the ribo isomer 20a, the 3-fluoro-L-ribo product 22, the 2,3-unsaturated L-hexose 21 and the erythro-2,3,4,6-tetradeoxy compound 23. The conformational feature, in solution, of the reported L-hexoses is also discussed on the basis of their 1H NMR data.
Databáze:	OpenAIRE
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