1038534-73-4Relevant academic research and scientific papers
Preparation of C-glycoside pendant β2 - and β2,2 -amino acids
Inaba, Yoko,Yano, Shigenobu,Mikata, Yuji
experimental part, p. 606 - 616 (2009/04/10)
Facile preparations of C-glycosyl β2- and β2,2-amino acids are described. Selective formation of a β-C-glycoside linkage was achieved by the reaction of a 2,3,4,6-tetra-O-acetyl-a-D-gluco/galactopyranosyl bromide (α-acetobromo- glucose/galactose) with the carbanion of a cyanoacetate ester. Crystallization selectively afforded one of two diastereomers with respect to the chiral center at the α-carbon of the side chain (C-2), however, this compound was found to epimerize during the following nitrile reduction. Separation of the diastereomers was achieved via the Fmoc derivatives. Diastereomerically pure C-glycosyl β2,2-amino acids were prepared by diastereoselective alkylation of C-glycosylated enolate, followed by nitrile hydrogenation. The present procedure serves as an efficient route to C-glycosylated β-amino acids containing a non-biodegradable linkage.
