239806-29-2

Upstream product

• 108957-20-6 (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester 
• 239806-28-1 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene 
• 51450-24-9 hexa-O-acetyl-D-maltal 
• 16004-15-2 1-bromomethyl-4-iodobenzene 

Downstream Products

• 239806-30-5 N^α-(tert-butoxycarbonyl)-C-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->4)-(2,3,6-tri-O-acetyl-α-D-mannopyranosyl)]-L-tyrosine benzyl ester 

Relevant academic research and scientific papers

C-Glycosyl Tyrosines. Synthesis and Incorporation into C-Glycopeptides

The synthesis of the Fmoc-protected C-glycosyl tyrosines 1 and 2, together with two other related C-glycosyl tyrosines, has been achieved. Key reactions involved (i) the reaction of a glycal with an organozinc reagent (carrying an aryl iodide function) in the presence of a Lewis acid to establish the C-glycosyl linkage and (ii) subsequent cross coupling of the aryl iodide to an alanyl zinc reagent (in the presence of a Pd(0) catalyst) to complete the construction of the α-amino acid moiety. Using solid-phase peptide synthesis methods, two units of the mannosyl derivative 1 (shown as L-Tyr-[C-Ac4-α-D-Man]) have been incorporated (with four units of glycine) into the linear hexapeptide 3 which was then converted to the C2-symmetric cyclic oligopeptide 4.