710307-00-9

Upstream product

• 10249-88-4 (S)-4-methyl-[(phenylmethyl)amino]pentan-1-ol 
• 590-17-0 cyanomethyl bromide 
• 100-52-7 benzaldehyde 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 

Downstream Products

• 873197-05-8 (2R,3S,4S)-(1-benzyl-2-cyano-4-isobutyl-azetidin-3-yl)-acetic acid ethyl ester 
• 873197-06-9 (2S,3S,4S)-(1-benzyl-2-cyano-4-isobutyl-azetidin-3-yl)-acetic acid ethyl ester 
• 873196-98-6 (2E,4S)-4-(benzyl-cyanomethyl-amino)-5-metyl-hept-2-enoic acid ethyl ester 
• 710307-03-2 [Benzyl-((R)-2-chloro-4-methyl-pentyl)-amino]-acetonitrile 

Relevant academic research and scientific papers

Stereocontrolled synthesis of 3-substituted azetidinic amino acids

A set of enantiomerically pure N-disubstituted β-amino alcohols was chlorinated by treatment with thionyl chloride. This reaction gave a mixture of regioisomeric chlorides that could be equilibrated to the more stable regioisomer by heating in DMF. The chlorides thus obtained were engaged in an intramolecular anionic ring-closure and gave access to fully protected enantio- and diastereomerically pure 2,3-cis-disubstituted azetidinic amino acids. One of the latter was deprotected and included in a short peptide sequence. Georg Thieme Verlag Stuttgart.

Azetidinic amino acids: Stereocontrolled synthesis and pharmacological characterization as ligands for glutamate receptors and transporters

A set of ten azetidinic amino acids, that can be envisioned as C-4 alkyl substituted analogues of trans-2-carboxyazetidine-3-acetic acid (t-CAA) and/or conformationally constrained analogues of (R)- or (S)-glutamic acid (Glu) have been synthesized in a diastereo- and enantiomerically pure form from ss-amino alcohols through a straightforward five step sequence. The key step of this synthesis is an original anionic 4-exo-tet ring closure that forms the azetidine ring upon an intramolecular Michael addition. This reaction was proven to be reversible and to lead to a thermodynamic distribution of two diastereoisomers that were easily separated and converted in two steps into azetidinic amino acids. Azetidines 35-44 were characterized in binding studies on native ionotropic Glu receptors and in functional assays at cloned metabotropic receptors mGluR1, 2 and 4, representing group I, II and III mGlu receptors, respectively. Furthermore, azetidine analogues 35, 36 and 40 were also characterized as potential ligands at the glutamate transporter subtypes EAAT1-3 in the FLIPR Membrane Potential (FMP) assay. The (2R)-azetidines 35, 37, 39, 41 and 43 were inactive in iGlu, mGlu and EAAT assays, whereas a marked change in the pharmacological profile at the iGlu receptors was observed when a methyl group was introduced in the C-4 position, compound 36 versus t-CAA. At EAAT1-3, compound 35 was inactive, whereas azetidines 36 and 40 were both identified as inhibitors and showed selectivity for the EAAT2 subtype. The Royal Society of Chemistry 2005.