606139-97-3

Upstream product

• 675832-36-7 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 113850-71-8 (S )-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoate 
• 73183-34-3 bis(pinacol)diborane 
• 70-78-0 3-Iodo-L-tyrosine 

Downstream Products

• 606139-98-4 5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid 
• 1086462-70-5 C₁₈H₃₂N₆O₃ 
• 1086462-68-1 H-His(5-Br)-Leu-Leu-NH₂ 
• 1086462-77-2 C₂₉H₄₅N₇O₆ 
• 1086462-78-3 C₂₈H₄₃N₇O₆ 
• 606139-99-5 C₁₅H₂₂BNO₇ 

Relevant academic research and scientific papers

Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage

A solid-phase strategy for the synthesis of biaryl cyclic peptides containing a side-chain to side-chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosin

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides.

Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling

Microwave irradiation efficiently promoted the solid-phase Suzuki-Miyaura reaction of a 5-bromohistidine with various arylboronic acids in the presence of a palladium catalyst. This methodology allowed the synthesis of peptides bearing a histidine residue substituted at position 5 of the imidazole ring with a phenyl, a substituted phenyl, a pyridyl, or a thienyl ring, as well as with the benzene ring of a tyrosine residue.

Synthesis of L,L-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids

Two types of cycloisodityrosines, 11 and 13, were synthesized from commercially available chiral tyrosine derivatives through the copper(II) acetate-DMAP-mediated diaryl ether formation of boronotyrosyltyrosines 8 and 10, respectively.