195005-73-3

Upstream product

• 218912-19-7 N-(tert-butyloxycarbonyl)-D-(3-iodo-4-methoxyphenyl)glycine methyl ester 
• 27460-85-1 N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 193073-85-7 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate 

Downstream Products

• 195005-81-3 [(R)-{[(2-Iodo-3,5-dimethoxy-benzylcarbamoyl)-methyl]-carbamoyl}-(3-iodo-4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester 
• 197723-36-7 (S)-2-[(R)-2-{2-[3-Bromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 250160-64-6 (S)-2-[(R)-2-{2-[3-Bromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 197723-38-9 (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester 
• 197723-40-3 (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester 
• 197723-32-3 (S)-2-[(R)-2-Amino-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 197723-30-1 (S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries

The synthesis of a bicyclic tripeptide that mimics the ABC ring system of vancomycin is described by using a ring closing metathesis (RCM) – peptide coupling – ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) strategy.

Total synthesis of vancomycin - Part 1: Design and development of methodology

o-Halosubstituted aromatic triazenes (e.g. I, Scheme 1) react with aryloxides (e.g. II, Scheme 1) in the presence of CuBr · Me2S, K2CO3 and pyridine in acetonitrile at reflux to afford biaryl ethers (e.g. V, Scheme 1). This general methodology (Tables 1 and 2) was applied to the construction of the C-O-D and D-O-E vancomycin model systems 37 (Scheme 2) and 50 (Scheme 3), demonstrating its potential in a projected total synthesis of vancomycin (1. Figure 1). For the construction of the vancomycin model AB biaryl ring system, a sequential strategy involving a Suzuki coupling of the C-O-D aryl iodide 74 (Scheme 7) and boronic acid 53 (Scheme 4), followed by macrolactamization was demonstrated, in which the preformed C-O-D ring framework served to preorganize the precursor for cyclization. The latter investigation led to Suzuki-coupling-based asymmetric synthesis of biaryl systems in which 2,2-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) was found to be the optimum ligand (Tables 3 and 4).