108149-66-2

Upstream product

• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 17257-71-5 (S)-Mosher acid 
• 108149-63-9 4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

The Synthesis and Configurational Stability of Differentially Protected β-Hydroxy-β-amino Aldehydes

Syntheses of 1,1-dimethylethyl (S)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (5) and 1,1-dimethylethyl (4S-trans)-4-formyl-2,2,5-trimethyl-3-oxazolidinecarboxylate (6) from commercially available serine and threonine derivatives are described.The method involves selective reduction of the corresponding oxazolidine esters 3 and 4 using diisobutylaluminum hydride at low temperature.These differentially protected β-hydroxy-α-amino aldehydes are also shown to be produced in 93-95 percent enantiomeric excess (via NMR and HPLC analysis of the Mosher esterderivatives 8 and epi-8)-thus making them useful as chiral, nonracemic synthons for asymmetric synthesis.

Efficient synthesis of a configurationally stable L-serinal derivative

An efficient synthesis of a configurationally stable L-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from L-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.