218912-19-7

Upstream product

• 27460-85-1 N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 193073-85-7 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate 
• 143323-49-3 (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate 
• 37763-23-8 D-2-p-hydroxyphenylglycine methyl ester 

Downstream Products

• 1197026-61-1 methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate 
• 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 

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.

Construction of the biaryl-part of vancomycin aglycon via atropo-diastereoselective Suzuki-Miyaura coupling

An atropo-diastereoselective synthesis with dr up to 98/2 towards the biaryl subunit of vancomycin based on the use of enantiopure β-hydroxysulfoxide derivatives as novel chiral auxiliary is reported.

Total synthesis of vancomycin - Part 2: Retrosynthetic analysis, synthesis of amino acid building blocks and strategy evaluations

Retrosynthetic analysis of vancomycin (1) defined vancomycin's aglycon (2) and protected triazene 3 (Figure 1) as advanced intermediates for an eventual total synthesis. Sequential assembly of 3 as shown in Figure 2 (strategy I) and Figure 3 (strategy II) led to amino acid building blocks 8-10 and 12-15, respectively, representing vancomycin's amino acids AA-1 to AA-7. These amino acid fragments were constructed by stereoselective routes and the two synthetic strategies were tested for feasibility. Strategy I, postulating construction of the vancomycin main framework in the order of D-O-E→D-O-E/C-O-D→D-O-E/C-O-D/A-B, suffered from serious epimerization problems at the AA-4 stereocenter; while strategy II, involving the sequence C-O-D→C-O-D/AB→C-O-D/AB/D-O-E proved viable. These findings set the stage for the final drive towards vancomycin's aglycon (2) and vancomycin (1).