120104-68-9

Upstream product

• 109745-70-2 methyl glyoxylate methyl hemi-acetal 
• 622-33-3 N-benzyloxyamine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 922-68-9 Methyl glyoxylate 

Downstream Products

• 95205-00-8 methyl 2-(benzyloxyamino)butanoate 
• 77426-68-7 methyl 2-(benzyloxyamino)-3-methylbutanoate 
• 95205-01-9 methyl 2-(benzyloxyamino)-4-methylpentanoate 
• 95205-02-0 N-(phenylmethoxy)phenylalanine methyl ester 
• 66642-18-0 N-(phenylmethoxy)alanine methyl ester 
• 669070-52-4 2-(phenylmethoxyamino)-4-pentenoic acid methyl ester 
• 928065-01-4 (2S,3S,4S)-3-hydroxy-4-[2-methoxy-2-oxo-1-[(phenylmethoxy)amino]ethyl]-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 1000205-23-1 methyl 2-(benzyloxyimino)-2-chloroacetate 

Relevant academic research and scientific papers

Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2- enylstannanes and 1-alkoxycarbonylimines and analogues: Stereoselective approaches to novel α-amino acids

Reactions of the allyltin trichloride 45 generated from (4S)-4-benzyloxypent-2-enyl(tributyl)stannane 1 with imines prepared from glyoxylates proceed with useful levels of 1,5-stereocontrol in favour of (4E)-2,6-anti-2-(alkylamino)-6-benzyloxyhept-4-enoat

Total synthesis of the large non-ribosomal peptide polytheonamide B

Polytheonamide B is by far the largest non-ribosomal peptide known at present, and displays extraordinary cytotoxicity (EC50 =68 pg ml -1 , mouse leukaemia P388 cells). Its 48 amino-acid residues include a variety of non-proteinogenic d- and l-amino acids, and the absolute stereochemistry of these amino acids alternate in sequence. These structural features induce the formation of a stable β-strand-type structure, giving rise to an overall tubular structure over 30A? in length. In a biological setting, this fold is believed to transport cations across the lipid bilayer through a pore, thereby acting as an ion channel. Here, we report the first chemical construction of polytheonamide B. Our synthesis relies on the combination of four key stages: syntheses of non-proteinogenic amino acids, a solid-phase assembly of four fragments of polytheonamide B, silver-mediated connection of the fragments and, finally, global deprotection. The synthetic material now available will allow studies of the relationships between its conformational properties, channel functions and cytotoxicity.

One-pot synthesis of α-amino acids based on free radical-mediated carbon-carbon bond formation

The one-pot reaction of 2-hydroxy-2-methoxyacetic acid methyl ester with benzyloxyamine and an alkyl radical provided a convenient method for preparing the protected α-amino acids via a carbon-carbon bond formation by intermolecular carbon radical additio