710307-03-2

Upstream product

• 710307-00-9 (S)-N-benzyl-N-cyanomethyl-leucinol 
• 100-52-7 benzaldehyde 
• 10249-88-4 (S)-4-methyl-[(phenylmethyl)amino]pentan-1-ol 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 

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.

Expeditive synthesis of homochiral fused tri- and tetrazoles-piperazines from β-amino alcohols

N-Cyanomethyl and N-propargyl β-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-piperazines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles.