RESUMO
A method for the protecting group free synthesis of ß-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding ß-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of ß-urea tethered amino acid-carbohydrate conjugates.
Assuntos
Glicoconjugados/síntese química , Glicosídeos/síntese química , Ureia/química , Acetilação , Glicoconjugados/química , Glicosídeos/química , Glicosilação , Espectroscopia de Prótons por Ressonância Magnética , SoluçõesRESUMO
The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three-component coupling strategy. The key steps involve the Heck-Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar 9. Glycosyl isocyanate 8 was prepared by the oxidation of isonitrile 10, which displayed excellent reactivity in the coupling event. Synthetic roadblocks, encountered during this synthetic effort, have led to the development of the alpha-selective, Lewis acid catalyzed phenyl glycosylation process with 2-amino-hexopyranose and a procedure for acetonide deprotection without affecting the silyl ethers.
