55325-57-0Relevant articles and documents
Optically Active 4-Oxaproline Derivatives: New Useful Chiral Synthons Derived from Serine and Threonine
Falorni. Massimo,Conti, Sandra,Giacomelli, Giampaolo,Cossu, Sergio,Soccolini, Francesco
, p. 287 - 294 (1995)
A very simple procedure for the preparation of chiral optically active N-protected-4-carboxy-1,3-oxazolidine (4-oxaproline) derivatives starting from serine and threonine is described which avoids the use of toxic solvents or reagents.Elaboration of these compounds allows significant improvement in the handling of serine and threonine during the multigram preparation of oligopeptide structures and affords versatile chiral building blocks for the organic synthesis.
Preparation of Oxazolidine-Containing Peptides: Unusual Effects in RhIII-Catalyzed Acetalizations of Aldehydes with Urethane-Protected Serine and Threonine Esters and with Dipeptides Containing Serine or Threonine Residues at the N-Terminus
Seebach, Dieter,Sommerfeld, Thimo L.,Jiang, Qiongzhong,Venanzi, Luigi M.
, p. 1313 - 1330 (2007/10/02)
The cyclization reaction of aldehydes with Z- and Boc-protected β-hydroxyamino-acid esters (Tables 1 and 2), or of dipeptides containing serine or threonine at the N-terminus (Table 3), to give oxazolidine derivatives, occurs in the presence of isopropyl orthoformate and catalytic amounts of (CF3SO3)3.The reaction may be carried out under kinetic or under thermodynamic control, so that the ratio of the two possible epimeric products can be changed.The protecting group can be removed from the 3-position of the oxazolidine ring, and the resulting NH group can be coupled with another amino acid.Thus, a new method for the preparation of peptides containing β-hydroxy-amino acid-derived oxazolidines ('pseudo-prolines') is available.N-Neopentyl-substituted tripeptides are also described.
