199467-15-7Relevant articles and documents
Triphenylphosphoranylidene substituted heterocycles as versatile intermediates
Katritzky, Alan R.,Vincek, Adam S.,Steel, Peter J.
experimental part, p. 1401 - 1423 (2009/07/17)
N-Cbz-(α-aminoacyl)benzotriazoles 5a-e reacted with (stabilized-methylene)triphenylphosphoranes 6 and 13 to give the corresponding esters 7a-e (66-91%) or nitriles 14a-e (63-85%). Deprotection of N-Cbz-γ-amino-β-oxo-α-triphenylphosphoranylidene esters 7a-
Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin
Wasserman, Harry H.,Petersen, Anders K.,Xia, Mingde
, p. 6771 - 6784 (2007/10/03)
Full details are given for the syntheses of the protease inhibitors, poststatin and eurystatin by the acyl cyanophosphorane coupling procedure used for the formation of α-keto amides. We have also extended this methodology to the syntheses of the related α-hydroxy amide natural products, phebestin, probestin and bestatin. The key step in the latter synthetic sequences involved diastereomeric selectivity in the reduction of the α-keto precursor to the corresponding α-hydroxy amide by the use of zinc borohydride.
Synthesis of cyanoketophosphoranes, precursors of β-amino-α-keto- esters from uncas
Paris, Marielle,Pothion, Catherine,Michalak, Christine,Martinez, Jean,Fehrentz, Jean-Alain
, p. 6889 - 6890 (2007/10/03)
Cyanomethylene triphenylphosphoranes of N-protected amino acids were synthesized from the corresponding N-urethane protected or amino acid N- carboxyanhydrides (UNCAs) by reaction with cyanomethyltriphenylphosphonium chloride in good yields. These compoun
