132149-66-7

Basic information

• Product Name: dimethyl 3,3′-(6,6′-dihydroxybiphenyl-3,3′-diyl)bis[2-(benzyloxycarbonylamino)propanoate]
• Synonyms: dimethyl 3,3′-(6,6′-dihydroxybiphenyl-3,3′-diyl)bis[2-(benzyloxycarbonylamino)propanoate]
• CAS NO: 132149-66-7
• Molecular Weight: 656.689
• Mol File: 132149-66-7.mol

Chemical Properties

• CAS DataBase Reference: dimethyl 3,3′-(6,6′-dihydroxybiphenyl-3,3′-diyl)bis[2-(benzyloxycarbonylamino)propanoate](CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 3,3′-(6,6′-dihydroxybiphenyl-3,3′-diyl)bis[2-(benzyloxycarbonylamino)propanoate](132149-66-7)
• EPA Substance Registry System: dimethyl 3,3′-(6,6′-dihydroxybiphenyl-3,3′-diyl)bis[2-(benzyloxycarbonylamino)propanoate](132149-66-7)

Safety Data

• Hazardous Substances Data: 132149-66-7(Hazardous Substances Data)

Upstream product

• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 

Downstream Products

• 1394296-04-8 (2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)-bis(2-(benzyloxycarbonylamino)propanoic acid) 
• 1394296-06-0 benzyl (2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)bis(1-(3-bromo-4-hydroxyphenethylamino)-1-oxopropane-3,2-diyl)dicarbamate 
• 1394296-07-1 (2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)-bis(2-amino-N-(3-bromo-4-hydroxyphenethyl)propanamide) 
• 79067-77-9 bastadin-3 
• 1394296-00-4 (2S,2′S)-dimethyl 3,3′-(5,5′-dibromo-6,6′-dihydroxybiphenyl-3,3′-diyl)bis(2-(benzyloxycarbonylamino)propanoate) 

Relevant articles and documents

PROCESS FOR MAKING BIARYL-BRIDGED CYCLIC PEPTIDES

The invention provides a method of preparing a biaryl-bridged cyclic peptide compound of Formula (I), where R1, R2, R3, R4, R5, R8, R7, R8, R9, R10, R11, R12, n and m are as defined in the specification. The biaryl-bridged cyclic peptides of Formula (I) are used in the preparation of pharmaceutically active substances, such as, for example, arylomycin and arylomycin analogues.

Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions

Biaryl-bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram-negative bacteria. Herein, we present a simple, flexible, and reliable strategy based on activating-group-assisted catalytic oxidative coupling for assembling biaryl-bridged cyclic peptides from natural amino acids. The synthetic approach was utilized for preparing a number of natural and unnatural biaryl-bridged cyclic peptides, including arylomycin/G0775 and RP 66453 cyclic cores.

First total synthesis of dioxepine bastadin 3

The synthesis of dioxepine bastadin 3, a tyrosine-tyramine derivative with a dibenzo-1,3-dioxepine scaffold that is rarely present among natural products, is described. The dibenzo-1,3-dioxepine ring was formed early in the sequence and the (E)-2-(hydroxy

Oxidative phenol coupling - Tyrosine dimers and libraries containing tyrosyl peptide dimers

The principles of phenol oxidation are outlined and summarized. Various procedures were used to dimerize tyrosine derivatives, especially linear tripeptides and cyclohexapeptides, via cross-linking of their phenolic side-chains. The coupling was performed by potassium hexacyanoferrate(III), phenyliodine(III)-bis(trifluoroacetate), vanadium(V)-oxyfluoride or horseradish peroxidase. The individual dityrosine and isodityrosine derivatives obtained in preparative scale, as well as the peptide-dimer libraries generated, were characterized by HPLC and electrospray ionization mass spectrometry. Further analyses were carried out by NMR spectroscopy, fluorescence spectroscopy and gas chromatography.

SYNTHESIS OF ANALOGUES OF THE BIPHENOMYCIN ANTIBIOTICS

The oxidative coupling of L-tyrosine derivatives with vanadium oxyhalides has given dityrosine intermediates which were cyclized to give analogues of the biphenomycin antibiotics.