126301-24-4Relevant academic research and scientific papers
Syntheses and Properties of Optically Active 2-Substituted Taurines
Higashiura, Kunihiko,Morino, Hiroe,Matsuura, Hirohide,Toyomaki, Yoshio,Ienaga, Kazuharu
, p. 1479 - 1481 (2007/10/02)
The synthesis of nine 2-substituted taurines (5a-i), including the marine natural product D-cysteinolic acid (5f), are described.These involve the successive conversion of N-t-butoxycarbonyl(Boc)-protected amino acid esters (1) into the N-Boc-2-aminoethanols (2), their O-mesylated derivatives (3), the deprotected 2-aminoethyl methanesulphonates (4), followed by the replacement of the mesyloxy group by a sulpho group to give the optically active taurines (5a-e,g-i).Hydrogenolysis of 2-benzyloxymethyltaurine (5e) gives D-cysteinolic acid (5f).The structure of another of the products, (5b), is also confirmed by an alternative synthesis from N-Boc-valine methyl ester (1b) via twoβ-bromoethylamine derivatives, (6b) and (7b).
