167264-35-9

Upstream product

• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 73899-15-7 1-(t-butyldimethylsilyloxy)-2-(4-bromophenyl)ethane 
• 4654-39-1 4-bromophenethanol 
• 167264-41-7 4-[2-(t-butyldimethylsilyloxy)ethyl]benzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1353660-68-0 C₃₉H₅₈N₄O₈Si 
• 1353660-72-6 C₃₈H₅₆N₄O₈Si 
• 1353660-78-2 C₅₃H₈₂N₄O₁₀Si 
• 1353660-33-9 (2S,3R)-methyl 3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2,3-dihydroxypropanoate 
• 1353660-41-9 (2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate 
• 1353660-50-0 (2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-methoxypropanoate 
• 1353660-59-9 (2S,3S)-methyl 3-amino-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-methoxypropanoate 

Relevant academic research and scientific papers

Synthesis of chondramide a analogues with modified β-tyrosine and their biological evaluation

Starting from cinnamates 9, obtained by Wittig reaction or Heck coupling, the diols 17 were prepared by asymmetric dihydroxylation. This was followed by a regioselective substitution of the 3-OH group with hydrazoic acid under Mitsunobu conditions. Methylation of the 2-OH group and reduction of the azide group led to the β-tyrosine derivatives 8. Condensation with the dipeptide acid 6 furnished the tripeptide part of the chondramides. The derived acids 21 were combined with the hydroxy ester 7 to the esters 22. Cleavage of the tert-butyl groups and intramolecular lactam formation gave rise to the chondramide A analogues 2 b-k. Growth inhibition assays showed most of the analogues to be biologically active. Some of them even reach the activity of jasplakinolide. It can be concluded that the 4-position of the aryl ring in the β-tyrosine of chondramide A tolerates structural modifications quite well.