174146-47-5

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 203504-61-4 (R)-(-)-(3,5-dihydroxy-4-methoxyphenyl)glycine 
• 212757-98-7 (3,5-Dihydroxy-4-methoxy-phenyl)-(2,2,2-trifluoro-acetylamino)-acetic acid methyl ester 
• 212758-01-5 (3,5-Dihydroxy-4-methoxy-phenyl)-(2,2,2-trifluoro-acetylamino)-acetic acid 
• 191542-08-2 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-methoxyphenyl)acetate 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 26973-43-3 (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid 
• 191542-10-6 (4S)-3-[2-(3,5-bis(benzyloxy)-4-methoxy)phenyl-1-oxoethyl]-4-(phenylmethyl)-2-oxazolidinone 
• 191542-07-1 (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid 
• 89936-31-2 methyl [3,5-bis(tert-butyldimethylsilyloxy)-4-methoxyphenyl]acetate 
• 54186-42-4 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid 
• 203504-59-0 4-Methyl-benzenesulfinic acid [(R)-(3,5-bis-benzyloxy-4-methoxy-phenyl)-cyano-methyl]-amide 
• 203504-58-9 4-Methyl-benzenesulfinic acid [(R)-cyano-(3,5-diisopropoxy-4-methoxy-phenyl)-methyl]-amide 
• 203504-55-6 4-Methyl-benzenesulfinic acid 1-(3,5-bis-benzyloxy-4-methoxy-phenyl)-meth-(Z)-ylideneamide 

Downstream Products

• 192328-54-4 (R)-(3-Bromo-4-methoxy-phenyl)-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-acetic acid methyl ester 
• 174146-48-6 (2S,3R)-2-{(R)-2-(3-Bromo-4-methoxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-acetylamino}-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 851912-48-6 C₅₇H₇₀N₆O₁₄Si 
• 691015-06-2 (R)-[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-(3,5-dichloro-4-methoxy-phenyl)-acetic acid benzyl ester 

Relevant academic research and scientific papers

Next-Generation Total Synthesis of Vancomycin

A next-generation total synthesis of vancomycin aglycon is detailed that was achieved in 17 steps (longest linear sequence, LLS) from the constituent amino acid subunits with kinetically controlled diastereoselective introduction of all three elements of atropisomerism. In addition to new syntheses of three of the seven amino acid subunits, highlights of the approach include a ligand-controlled atroposelective one-pot Miyaura borylation-Suzuki coupling sequence for introduction of the AB biaryl axis of chirality (>20:1 dr), an essentially instantaneous and scalable macrolactamization of the AB ring system nearly free of competitive epimerization (>30:1 dr), and two room-temperature atroposelective intramolecular SNAr cyclizations for sequential CD (8:1 dr) and DE ring closures (14:1 dr) that benefit from both preorganization by the preformed AB ring system and subtle substituent effects. Combined with a protecting group free two-step enzymatic glycosylation of vancomycin aglycon, this provides a 19-step total synthesis of vancomycin. The approach paves the way for large-scale synthetic preparation of pocket-modified vancomycin analogues that directly address the underlying mechanism of resistance to vancomycin.

Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents

The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, 'EtAl(OR)CN' to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.

Expeditious syntheses of two arylglycine derivatives corresponding to the central amino acid of the vancomycin family of antibiotics

Two expeditious and efficient syntheses (in 7 and 4 steps, respectively) are described for the central amino acid part of the vancomycin family. The first method constitutes a concise asymmetric synthesis, starting from 4- hydroxyphenylacetic acid, of (R)-(3,5-dihydroxy-4-methoxyphenyl)glycine derivatives using Evans' asymmetric azidation methodology. In the second approach, an efficient synthesis of a protected 3,5-dichloro-4- methoxyphenylglycine derivative is described, starting from commercially available (R)-4-hydroxyphenylglycine. These two syntheses are much shorter and operationally simpler than those previously described, and are currently employed in an effort towards the construction of the bicyclic system of vancomycin and ristocetin.