610314-16-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 610314-22-2 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-[4-(2,6-dichloro-benzyloxy)-phenyl]-propionic acid methyl ester 
• 1342305-95-6 N-[(S)-2-chloropropionyl]-N-p-methoxybenzyl-L-Tyr(2,6-dichlorobenzyl)-OMe 
• 1342305-97-8 (3S,4S)-4-p-(2,6-dichlorobenzyloxy)benzyl-1-p-methoxybenzyl-4-methoxycarbonyl-3-methyl-2-azetidinone 
• 1342305-99-0 (3S,4S)-4-carboxy-4-p-(2,6-dichlorobenzyloxy)benzyl-1-p-methoxybenzyl-3-methyl-2-azetidinone 
• 1342306-05-1 (3S,4S)-4-p-(2,6-dichlorobenzyloxy)benzyl-1-p-methoxybenzyl-3-methyl-4-[2-(piperidin-1-yl)ethyl]carbamoyl-2-azetidinone 

Relevant academic research and scientific papers

Optically active 1,3,4,4-tetrasubstituted β-lactams: Synthesis and evaluation as tumor cell growth inhibitors

The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted β-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the β-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted β-lactams are reported here.

Memory of chirality in the stereoselective synthesis of β-lactams: Importance of the starting amino acid derivative

The enantioselectivity of the base-promoted cyclization of N-alkyl-N-chloroacetyl amino acid derivatives to β-lactams is dependent on the substituents on the starting material. While tBu esters are preferred over Me esters, and N-Bzl-, N-Pmb, N-Nph and N-Mom groups gave similar e.e. values, only amino acid derivatives with branched side-chains at the γ-position were able to show a good memory of chirality.