75880-46-5Relevant articles and documents
Improved synthetic access to the β,γ-enol ether amino acids, L-2-amino-4-methoxy-trans-but-3-enoic acid and 1-2-amino-4-methoxy-cis-but-3-enoic acid
Alks, Vitauts,Sufrin, Janice R.
, p. 5257 - 5260 (1990)
A synthetic route to L-2-amino-4-methoxy-trans-but-3-enoic acid, exclusive of the cis-isomer, has been developed. The key step is direct formation of a trans-enol ether derivative from the corresponding dimethylacetal, by refluxing in CCl4, in the presence of hexamethyldisilazane and Me3SiI. The isomeric L-cis amino acid could be accessed from this route by isomerizing the intermediate, methyl DL-2-acetamido-2-amino-4-methoxy-trans-but-3-enoate at 217° C to give cis-trans mixture in a 1:10 ratio.