848047-83-6Relevant articles and documents
Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups
Tanaka, Hiroshi,Iwata, Yuki,Takahashi, Daisuke,Adachi, Masaatsu,Takahashi, Takashi
, p. 1630 - 1631 (2005)
The efficient and elegant synthesis of N-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosyl N-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane
2-Phenyl-tetrahydropyrimidine-4(1H)-ones - Cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids
Nahrwold, Markus,Stoncius, Arvydas,Penner, Anna,Sewald, Norbert,Neumann, Beate,Stammler, Hans-Georg
supporting information; experimental part, (2010/04/22)
Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-β2-homoaspartate.