230973-45-2Relevant academic research and scientific papers
Synthesis of β,β-dimethylated amino acid building blocks utilizing the 9-phenylfluorenyl protecting group
Kawahata, Noriyuki,Weisberg, Michael,Goodman, Murray
, p. 4362 - 4369 (2007/10/03)
Optically pure β,β-dimethylated amino acid building blocks with functionalized side chains have been prepared from D-aspartic acid. The dimethylation was accomplished by regioselective dialkylation of 9- phenylfluorenyl (PhFl)-protected aspartate diesters. The bulk of the PhFl protecting group also allowed for a variety of functional group manipulations to be carried out on the side chain without affecting the C(α) ester of the aspartate. As a result, the derivatives of the following novel amino acids were synthesized in this study: β,β-dimethyl-D-aspartic acid, β,β- dimethyl-D-homoserine, 3,3-dimethyl-D-2,4-diaminobutyric acid, β,β- dimethyl-D-lysine, β,β-dimethyl-D-homoglutamate, β,β-dimethyl-D- ornithine, and 3,3-dimethylazetidine-2-carboxylic acid. The β,β- dimethylated amino acids were synthesized in high enantiomeric excess as determined by coupling the novel building blocks to chiral reagents.
