171738-31-1Relevant articles and documents
Synthesis of β-amino-α-hydroxy esters and β-amino-α- azido ester by sharpless asymmetric aminohydroxylation, byproducts analysis
Liu, Zuosheng,Ma, Nianchun,Jia, Yanxing,Bois-Choussy, Michele,Malabarba, Adriano,Zhu, Jieping
, p. 2847 - 2850 (2007/10/03)
(Chemical Equation Presented) Synthesis of enantiomerically pure β-amino-α-hydroxy esters (1, 2) and β-amino-α-azido ester (3) using Sharpless AA as a key step is described. A hitherto unreported side reaction, the oxidation of the β-hydroxy-α-amino ester
Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents
Davis, Franklin A.,Fanelli, Dean L.
, p. 1981 - 1985 (2007/10/03)
The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, 'EtAl(OR)CN' to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.
Asymmetric Synthesis of (2S,3R) β-(4-F-3-NO2) phenyl Serine, D-(R)-4-methoxy-3,5-Bis tButyldimethylsiloxy Phenylglycine and Their Assemblage to C-O-D Ring of Vancomycin
Zhu, Jieping,Bouillon, Jean-Philippe,Singh, Girij Pal,Chastanet, Jacqueline,Beugelmans, Rene
, p. 7081 - 7084 (2007/10/02)
The asymmetric synthesis of two appropriately functionalyzed non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described.The assemblage of these amino acids into linear tripeptide followed by biary ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring vancomycin.