951174-19-9

Upstream product

• 27784-76-5 tert-butyl diethylphosphonoacetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 
• 53484-52-9 3-(4-methoxyphenyl)-acrylic acid tert-butyl ester 
• 53484-52-9 tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate 

Downstream Products

• 873326-22-8 tert-butyl (3R)-3-amino-3-(4-methoxyphenyl)propanoate 
• 131690-57-8 (R)-β-amino-β-(4-methoxyphenyl)propionic acid 

Relevant academic research and scientific papers

Asymmetric synthesis of syn- and anti-α-deuterio-β3- phenylalanine derivatives

The conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl) amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium β-amino enolates with D2O provides access to anti configured α-deut

Synthesis, in vitro and in vivo biological evaluation, docking studies, and structure-activity relationship (SAR) discussion of dipeptidyl boronic acid proteasome inhibitors composed of β-amino acids

A series of novel dipeptidyl boronic acid proteasome inhibitors composed of β-amino acids were synthesized, in vitro and in vivo biologically evaluated, and theoretically modeled for the first time. From the screened racemic compounds in enzyme, 4i was the most active. The IC50 value of its pure enantiomer 4q was 9.6 nM, 36-fold more active than its isomer 4p and as active as the marketed bortezomib in inhibiting human 20S proteasome. This candidate also showed good activities with IC50 values nearly less than 5 μM against several human solid and hematologic tumor cell lines. Safety evaluation in vivo with zebrafish and Sprague-Dawley (SD) rats showed that the candidate 4q was less toxic than bortezomib. Pharmacokinetic profiles suggested candidate 4q showed a more plasma exposure and longer half-life than bortezomib. Docking results indicated that 4q nearly interacted with 20S proteasome in a similar way as bortezomib.

Parallel synthesis of homochiral β-amino acids

The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.