Synthesis Of Enantiopure Free And N-Benzyloxycarbonyl Protected3-Substituted Homotaurines From Naturally Occurring Amino Acids

Homotaurine,3-amino-1-propanesulfonic acid, has been widely investigated for its importantly biological activities and medicinal values. Several synthetic methods of non-substituted, mono-substituted and mutiple-substituted homotaurines have been developed, but general method of enantiopure3-substituted homotaurines has not been reported till now. It is important to synthesize of specially configurational3-substituted homotaurines.Enantiopure N-benzyloxycarbonyl-protected and free3-substituted homotaurines were synthesized from naturally occuring amino acids. Enantiopure N-Cbz-3-substituted homotaurines were prepared via the protection of amino acids with benzylchloroformate, and then transformation to diazoketone with dizomethane, subsequent Arndt-Eistert homologation, reduction, nucleophilic substitution and oxidation. The3-substituted homotaurines were synthesized using Pd/C catalytic hydrogenolysis of N-Cbz-3-substituted homotaurines.An effective synthetic method for enantiopure N-benzyloxycarbonyl-protected and free3-substituted homotaurines from naturally occuring amino acids is described. There are several advantages to this method:1) commercial availability of reagents;2) mild reaction conditions;3) easy operation;4) moderate to high reaction efficiency and unaffected by water. The current method is a convenient and practical method for the synthesis of enantiopure3-substituted homotaurin.es with moderate to good yields.