145790-72-3Relevant academic research and scientific papers
Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
Loke, Inga,Park, Natja,Kempf, Karl,Jagusch, Carsten,Schobert, Rainer,Laschat, Sabine
supporting information; experimental part, p. 697 - 704 (2012/01/05)
α-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of β-oxo functionalized α-aminoesters, e.g., esters of serine, threonine or β-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the β-OR group and on the configuration of β-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides.
Novel serine-based linker for the solid-phase synthesis of organic compounds
Chou, Yuo-Ling,Morrissey, Michael M.,Mohan, Raju
, p. 757 - 760 (2007/10/03)
A novel serine-derived linker has been developed that allows phenolic templates to be cleaved from the resin with fluoride ion. The linker is stable to acids such as TFA and bases such as pyrrolidine. The linker should provide utility in multi-step solid phase organic chemistry protocols where both acid and base chemistry is used.
Protection of Hydroxy Groups by Silylation: Use in Peptide Synthesis and as Lipophilicity Modifiers for Peptides
Davies, John S.,Higginbotham, Clement L.,Tremeer, E. John,Brown, Charles,Treadgold, Richard C.
, p. 3043 - 3048 (2007/10/02)
A survey of a series of organosilyl derivatives of serine and tyrosine has shown that they have a satisfactory stability profile for use in peptide synthesis.Only when alkaline conditions were used did side-reactions appear.A range of stability profiles have been determined from a study of organosilyl derivatised dipetides under different conditions, giving t1/2 values for hydrolysis ranging from 41 to 465 min in acid conditions, yet giving long-term stability at pH-values near to neutrality.
