885019-64-7

Upstream product

• 262266-33-1 1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol 
• 217326-89-1 N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester 

Downstream Products

• 885019-68-1 N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester 
• 885019-67-0 N-[(1,1-dimethylethoxy)carbonyl]-4-(3,4,6-tri-O-acetyl-1,2-dideoxy-D-arabino-hexenopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester 

Relevant academic research and scientific papers

Gram-scale preparation of a p-(C-glucopyranosyl)-L-phenylalanine derivative by a negishi cross-coupling reaction

A p-(C-glucopyranosyl)-L-phenylalanine derivative protected to be directly incorporated into a peptidic chain is prepared in 37 % yield from glucose on a gram scale, with a Negishi cross-coupling reaction as the key step. Zincated glucal and p-iodo-L-phenylalanine are involved in this organometallic coupling, which gives rise to a link between the sugar and amino acid moieties in 90 % yield; the β-gluco configuration of the C-glycopyranosyl amino acid is ascertained by a stereoselective hydroboration of the double bond of the glucal. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.