97206-21-8

Upstream product

• 95260-65-4 (2R,4R)-4-Benzyl-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 17350-84-4 (R)-2-amino-2-methyl-3-phenylpropanoic acid 
• 565234-19-7 benzyl (2S,3R,5R)-2,3-dimethoxy-2,3,5-trimethyl-6-oxomorpholine-4-carboxylate 
• 2448-45-5 Cbz-D-Phe 
• 565234-26-6 benzyl (2S,3R,5R)-5-benzyl-2,3-dimethoxy-2,3,5-trimethyl-6-oxomorpholine-4-carboxylate 
• 100-39-0 benzyl bromide 
• 131288-30-7 (2R,4R)-3-Benzyloxycarbonyl-2-phenyl-4-phenylmethyl-5-oxooxazolidine 

Downstream Products

• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 711015-15-5 Cbz-D-(α-Me)Phe-NH-t-Bu 
• 515871-94-0 4-[N',N''-bis(tert-butyloxycarbonyl)guanidino]phenyl N-(benzyloxycarbonyl)-α-methyl-D-phenylalaninate 

Relevant academic research and scientific papers

Role of secondary structure in the asymmetric acylation reaction catalyzed by peptides based on chiral Cα-tetrasubstituted α-amino acids

In a recent series of papers, Miller and co-workers were able to show that His(π-Me)-based, terminally protected peptides are potent catalysts of the asymmetric acyl transfer reaction, useful for the kinetic resolution of alcohols. In a structure-supporting solvent, one of the most active compounds, an Aib-containing tetrapeptide, is folded in a doubly intramolecularly H-bonded β-hairpin motif incorporating a type-II′ β-turn conformation. In this work, we have expanded the study of the Miller tetrapeptide by examining a set of analogues and shorter sequences (dipeptide amides), characterized by chiral Cα-tetrasubstituted α-amino acids of diverging bulkiness and optical configuration. Peptide synthesis in solution, conformational analysis by FT-IR absorption and 1H NMR techniques, and screening of catalytic activity as well have been performed. Our results confirm the close relationship between the β-hairpin 3D-structure and the catalytic activity of the peptides. A tetrapeptide analogue slightly more selective than the Miller compound has been found. However, the terminally protected, industrially more appealing, dipeptide amides are poorly effective.

A 2,3-butanedione protected chiral glycine equivalent--a new building block for the stereoselective synthesis of enantiopure N-protected alpha-amino acids.

A new chiral glycine equivalent 7 has been synthesised from glycidol using a chiral memory protocol, and its use in the synthesis of N-Z protected alpha-amino acids was demonstrated in a series of diasteroselective lithium enolate alkylation reactions and subsequent acid hydrolyses.

Process for preparation of alpha-alkyl amino acids

A process for preparing α-alkyl amino acids by enantioretentive α-alkylation of α-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.

ENANTIORETENTIVE ALKYLATION OF ACYCLIC AMINO ACIDS

A stereospecific method is described for the alkylation of acyclic amino acids (alanine and phenylalanine) which proceeds with retention of configuration.The method involves a) conversion of the amino acid to the predominantly cis 2-aryl-3-carbobenzyloxy oxazolidinones (2 and 8), b) alkylation of the potassium enolate with CH3I or PhCH2Br, c) base hydrolysis and hydrogenolysis to afford the alkylated amino acid.