128369-70-0

Upstream product

• 67-56-1 methanol 
• 90508-28-4 N-allyloxycarbonyl-L-alanine 
• 107-18-6 allyl alcohol 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 2937-50-0 Allyl chloroformate 

Downstream Products

• 19794-10-6 (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 
• 132402-82-5 (S)-1-((S)-2-{[2-((S)-1-Allyloxycarbonylamino-ethyl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 10065-72-2 L-Alanine methyl ester 
• 59724-69-5 (S)-N-tosylalanine methyl ester 

Relevant academic research and scientific papers

Palladium-catalyzed transprotection of allyloxycarbonyl-protected amines: Efficient one-pot formation of amides and dipeptides

The synthetic utility of the N-(allyloxycarbonyl) (Alloc) substituent in α-amino acid derivatives is substantially extended beyond its well-known function as an amine protecting group. When the palladium-catalyzed deprotection is carried out by using tributyltin hydride as nucleophile (the Guibe method) in the presence of an active acylating agent a new acyl group is introduced on nitrogen. Successful acylating agents include carboxylic acid anhydrides, acid chlorides, and activated esters. A useful example of this methodology is the removal of the Alloc group in the presence of tert-butyl dicarbonate, which in essence amounts to a 'transprotection' to a Boc-protected α-amino acid derivative. More importantly, the use of activated N-protected α-amino ester derivatives (e.g., pentafluorophenyl esters) leads to dipeptides. This new method for peptide coupling proceeds very fast under mild conditions, in good to excellent yields, and without noticeable racemization.

Urethanes synthesis from oxamic acids under electrochemical conditions

Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.

Substrate-directed lewis-acid catalysis for peptide synthesis

A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: (1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; (2) the reaction proceeds without any racemization; (3) the new substrate-directed chemical ligation using the titanium catalyst is applicable to convergent peptide synthesis. These advantages overcome some of the unresolved problems in classical peptide synthesis.

Synthetic studies towards cyclic peptides. Concise synthesis of thiazoline and thiazole containing amino acids

Concise and efficient syntheses of optically pure thiazoline and thiazole containing amino acids of the constitution (26) and (27), based on simple condensation reactions between cysteine esters and N-protected imino ethers (22) and (25) derived from chir