218769-48-3

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 71400-62-9 O^4'-Benzyl-3'-iod-L-tyrosin 
• 100-39-0 benzyl bromide 
• 71400-63-0 N-tert-butyloxycarbonyl-3-iodo-L-tyrosine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 691394-91-9 methyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 119336-08-2 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 
• 70-78-0 3-Iodo-L-tyrosine 

Downstream Products

• 218769-34-7 [(S)-2-(4-Benzyloxy-3-iodo-phenyl)-1-((S)-1-{4-cyano-5-[1-(2-hydroxy-phenyl)-vinyl]-oxazol-2-yl}-2-methyl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 405906-76-5 (2S,7S,10S)-10-Amino-15-benzyloxy-2-[2-(2-bromo-ethoxy)-phenyl]-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaene-4-carbonitrile 
• 405906-74-3 {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-yl}-carbamic acid tert-butyl ester 
• 405906-79-8 [(2R,7S,10S)-15-Benzyloxy-4-cyano-2-hydroxymethyl-2-(2-hydroxy-phenyl)-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl]-carbamic acid benzyl ester 
• 405906-77-6 {(2S,7S,10S)-15-Benzyloxy-2-[2-(2-bromo-ethoxy)-phenyl]-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl}-carbamic acid benzyl ester 
• 405906-80-1 [(2R,7S,10S)-15-Benzyloxy-2-(3-bromo-2-hydroxy-phenyl)-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl]-carbamic acid benzyl ester 
• 405906-75-4 {(2S,3S,8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,4,6,13⁽¹⁷⁾,14-pentaen-11-yl}-carbamic acid tert-butyl ester 
• 405906-78-7 {(2R,7S,10S)-15-Benzyloxy-2-[2-(2-bromo-ethoxy)-phenyl]-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl}-carbamic acid benzyl ester 
• 918304-78-6 C₃₈H₄₁IN₄O₆ 
• 1373311-93-3 (4²S,4⁵S)-1⁶,2⁶-bis(benzyloxy)-4(2,5)-piperazina-1,2(1,3)-dibenzenacyclopentaphane-4³,46-dione 

Relevant academic research and scientific papers

Scalable Synthesis of Mycocyclosin

We report herein the scalable total synthesis of the secondary metabolite, mycocyclosin, initially isolated from Mycobacterium tuberculosis. Mycocylosin bears a highly strained 3,3′-dityrosine biaryl system which arises biosynthetically from an intramolec

LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs

The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has been found to be up-regulated in many different tumor types, and its expression levels have been correlated with prognosis. Substitution at the meta position of aromatic amino acids has been reported to increase affinity for LAT-1; however, the SAR for this position has not previously been explored. Guided by newly refined computational models of the binding site, we hypothesized that groups capable of filling a hydrophobic pocket would increase binding to LAT-1, resulting in improved substrates relative to parent amino acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted phenylalanine and tyrosine analogs is described.

Total synthesis of nominal diazonamides - Part 1: Convergent preparation of the structure proposed for (-)-diazonamide A

Unable to bear the weight of scrutiny, the original structure proposed for (-)diazonamide A (1) must be revised. A convergent, stereocontrolled total synthesis provided 1, which shows altered physical and spectroscopic characteristics relative to those of