Bohnstedt, Adolph C.; Prasad, J. V. N. Vara; Rich, Daniel H. published their research in Tetrahedron Letters on August 13 ,1993. The article was titled 《Synthesis of E- and Z-alkene dipeptide isosteres》.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The article contains the following contents:
The syntheses of MeLeu-Leu and MeLeu-D-Leu alkene dipeptide isosteres (E)-I and (E)-II (Boc = Me3CO2C, R = H), and (Z)-I and (Z)-II (R = Me) are described. (E)-I and (E)-II were synthesized stereoselectively by employing the [2,3]-Wittig rearrangement to control double bond geometry and C-2 configuration. (Z)-I and (Z)-II were obtained as an easily separable mixture of diastereomers via alkylation of a Z-alkene MeLeu-Gly isostere that was obtained using a Z-selective Wittig reaction as the key step. All isosteres are isolated with high stereochem. purity. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)
(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics