126301-32-4Relevant academic research and scientific papers
A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines
Chen, Ning,Jia, Weiyi,Xu, Jiaxi
experimental part, p. 5841 - 5846 (2010/03/03)
Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid, oxidation of the thiazolidine-2-thione intermediates generated from, vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines.
Expeditious and practical synthesis of various substituted taurines from amino alcohols
Zhang, Wei,Wang, Boyuan,Chen, Ning,Du, Da-Ming,Xu, Jiaxi
, p. 197 - 200 (2008/12/20)
Various substituted taurines have been synthesized expeditiously and practically in satisfactory to good yields directly from amino alcohols using a two-step, one-pot procedure, in which the amino alcohols undergo sulfuric acid esterification and subsequent sodium sulfite substitution. Treatment of amino-substituted secondary alcohols using the same procedure gave 2-substituted or 1,2-disubstituted taurines, indicating the formation of aziridines as intermediates during the substitution step. This method is one of the most efficient routes for preparing structurally diverse 2-substituted and 1,2- and 2,2-disubstituted taurines. Georg Thieme Verlag Stuttgart.
Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines
Hu, Libo,Zhu, Hui,Du, Da-Ming,Xu, Jiaxi
, p. 4543 - 4546 (2008/02/05)
(Chemical Equation Presented) Taurine and substituted taurines were synthesized efficiently from aziridines via ring-opening reaction with thioacetic acid, oxidation with performic acid, and hydrolysis in hydrochloric acid. The current method shows more benefit in purification and efficiency in the preparation of taurine and structurally diverse 2-substituted, 2,2-disubstituted, and 1,2-, 2,2-, and 2,N-alkylene taurines.
A new and expeditious asymmetric synthesis of (R)- and (S)-2-aminoalkanesulfonic acids from chiral amino alcohols
Xu, Jiaxi
, p. 1129 - 1134 (2007/10/03)
The mechanism for the transformation of β-amino alcohol methanesulfonate hydrochlorides into sodium β-amino alkanesulfonates using sodium sulfite was investigated. The results show that sodium sulfite initially neutralizes the β-amino alcohol methanesulfonate hydrochloride to give a free β-amino alcohol methanesulfonate, which then cyclizes to a 2-alkylaziridine. Attack by the previously formed sodium bisulfite at the less hindered carbon atom of the aziridine ring then yields a β-amino alkanesulfate sodium salt. Based on this mechanistic proposal, a new and rapid asymmetric synthesis of (R)- and (S)-2-aminoalkanesulfonic acids from chiral amino alcohols was developed. Chiral amino alcohols were converted to chiral aziridines through the Wenker method or Mitsunobu reaction and the resulting aziridines were reacted with sodium bisulfite to produce chiral β-amino alkanesulfonic acids.
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).
