3695-68-9Relevant academic research and scientific papers
Efficient synthesis of benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω- iodoalkanoates
Koseki, Yohei,Yamada, Haruka,Usuki, Toyonobu
experimental part, p. 580 - 586 (2011/06/21)
The efficient synthesis of four benzyl 2-(S)-[(tert-butoxycarbonyl)amino]- ω-iodoalkanoates {benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-3- iodopropanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-4-iodobutanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-
Synthesis of L-selenocystine, L-[77Se]selenocystine and L-tellurocystine
Stocking, Emily M.,Schwarz, Jessie N.,Senn, Hans,Salzmann, Michael,Silks, Louis A.
, p. 2443 - 2447 (2007/10/03)
Synthetic routes for the synthesis of stable isotope labelled amino acids which contain either a selenium or a tellurium atom have been explored. L-Selenocystine, L-[77Se]selenocystine and L-tellurocystine have been constructed in four steps from commercially available methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionate. The sequence of reactions has been successfully scaled up giving significant quantities of the chalcogen based amino acids in fair to good overall yield. Copyright 1997 by the Royal Society of Chemistry.
Preparation of Enantiomerically Pure Protected 4-Oxo-α-amino Acids and 3-Aryl-α-amino Acids from Serine
Jackson, Richard F. W.,Wishart, Neil,Wood, Anthony,James, Keith,Wythes, Martin J.
, p. 3397 - 3404 (2007/10/02)
The organozinc reagent 13, prepared from the protected β-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-α-amino acids 17 in 39-90percent yield (13 examples).Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67percent yield (11 examples).The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.
