Synthesis And Chiral Recognition Performance Evaluation Of Trehalose Phenylcarbamate Derivatives

Cellulose and amylose polysaccharide derivatives have excellent chiral recognition properties and have been widely used in the preparation of chiral stationary phases for high performance liquid chromatography(HPLC).As a natural disaccharide different from traditional polysaccharides,trehalose has glucopyranose unit and ?-1,1 glycosidic bond offering trehalose unique structural characteristics.This property,together with the low cost advantage of trehalose,exhibit a great potential as a natual and renewable resource to develop a new type of chiral stationary phase with high chiral recognition.Based on this research background,this topic has carried out research on the synthesis of trehalose phenylcarbamate derivatives and further explored the chiral recognition performance and influencing factors of trehalose derivatives.First,a series of novel trehalose phenylcarbamate derivatives with different substituents on the benzene ring and trehalose phenylcarbamate derivatives with different proportions of triethoxysilylpropyl were synthesized by one-pot method.The structure and degree of substitution of the derivatives were characterized by ~1H NMR and FT-IR.Then,based on trehalose derivatives,we prepared coated and bonded chiral stationary phases,use TGA to determine the coating rate and bonding rate of the chiral stationary phase,and prepared high performance liquid chromatography columns by homogenization.Finally,based on the chiral stationary phase,we used high performance liquid chromatography to perform chiral resolution of 9 typical chiral compounds to evaluate the chiral recognition performance of the synthesized trehalose derivatives.And under different elunts,we compared the chiral recognition performance of the prepared coated and bonded trehalose chiral stationary phases.The results show that a series of trehalose phenyl carbamate derivatives have been successfully synthesized in this paper,and the coating rate and bonding rate of the prepared coated and bonded chiral stationary phases meet the experimental requirements.Trehalose phenylcarbamate derivatives can achieve effective chiral resolution of the chiral compounds Rac-6,Rac-7 and Rac-9,and the chiral recognition performance of Rac-6 and Rac-7 are better than the commercial chiral columns Chiralcel OD and Chiralpak AD.It shows that the trehalose phenylcarbamate derivatives synthesized have special recognition advantages for metal complexes and ketone chiral compounds.Its chiral recognition performance is mainly affected by the electronegative effect,position and steric hindrance of the substituents on the benzene ring.In addition,comparing the chiral recognition performance of the coated and immobilized trehalose chiral stationary phases,the latter is significantly better than the former for the chiral compounds Rac-1 and Rac-4.And under the condition of polar mobile phase(H/C=70/30,v/v),the chiral recognition performance of the immobilized trehalose chiral stationary phase CSP-Tre-2a for Rac-1 and Rac-4 get a significant improvement.The separation factors?are as high as 3.77 and 2.13,which are significantly better than the commercial chiral column Chiralpak IA.It reflects the chiral recognition advantage of the bonded trehalose chiral stationary phase prepared in this article.