351340-22-2

Upstream product

• 277331-22-3 (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-2-azetidinone 
• 351340-72-2 Benzyl-[(S)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-prop-(E)-ylidene]-amine 
• 143159-97-1 (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone 
• 19810-31-2 Benzyloxyacetyl chloride 
• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 150949-66-9 (+)-(3R,4R)-cis-1-benzyl-3-benzyloxy-4-formyl-2-azetidinone 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 162779-98-8 (S)-1-Benzyl-4-ethyl-azetidine-2,3-dione 
• 162779-92-2 (3R,4S)-1-Benzyl-4-ethyl-3-hydroxy-azetidin-2-one 

Relevant academic research and scientific papers

A β-lactam-based stereoselective access to β,γ-dihydroxy α-amino acid-derived peptides with either α,β-like or unlike configurations

A concise access to α,β-dihydroxy α-amino acid-derived N-carboxy anhydrides (NCAs) with either like or unlike relative configuration is described. The key steps of the synthetic route are the preparation of the nonracemic 4-alkenyl β-lactams, through either Homer-type olefination of a common 4-formyl β-lactam or the Corey-Winter alkene synthesis applied to 4-dihydroxyalkyl β-lactams, followed by the Sharpless AD reaction, and a subsequent ring expansion of the corresponding 4-substituted 3-hydroxy β-lactams promoted by TEMPO. The opening of thus-prepared NCAs upon treatment with different O- and N-nucleophiles, including α-amino esters which lead to peptides, has also been studied under various reaction conditions.

A β-Lactam Framework as a β-Alanyl Dication Equivalent: New Synthesis of α-Amino Acid N-carboxy Anhydrides (NCAs) Derived from β-Substituted Alanines

Optically pure 4-formyl-3-hydroxy β-lactams are transformed into 4-methylaryl and 4-(2-ethylaryl) derivatives and converted into β-substituted alanine-derived NCAs through oxidation and Baeyer-Villiger rearrangement of the resulting α-keto β-lactams.