Studies On The Synthesis Of L,4-Substituted-1,2,3-Triazole Of β-Cyclodextrin Derivatives Via Click Reaction

Cyclodextrins（CDs） are widely examined as typical example of organic hostcompounds.The CD molecules are cyclic oligosaccarides containing six to thirteenanhydroglucose units joined by α-1,4glucosidic linkages. Cyclodextrins havesignificant potential as drug carriers arising from their ability to form inclusioncomplexes with hydrophobic guest molecules. The potential utility of such inclusionphenomena includes solubilization,encapsulation and transport of biologically activemolecules. Modified cyclodextrins not only extend and improve the originalmolecular binding ability，but also alter the molecular selectivity. Click chemistry is apratical way to synthesize new compounds that refers to the rapid synthesis and theuse of cheap raw materials which are also readily available. Nowadays,the mostattractive click reaction is the Cu（I）-catalyzed Huisgen1,3-dipolar cycloaddition（CuAAC） of azides and terminal alkynes to afford1,4-substituted-1,2,3-triazoles.1,2,3-Triazoles are important N-heterocyclic compounds, which have been used inwide areas such as material science, pharmaceutical synthesis and biologicalconjugation. In addition, a number of compounds containing1,2,3-triazoles haveshown a broad spectrum of biological activities such as herbicidal, antibacterial,antiallergic,fungicidal and anti-HIV. Moreover, the modification of CDs throughCu（I）-catalyzed Huisgen1,3-dipolar cycloaddition reaction also provides a newmethod to synthesize the cyclodextrin derivatives effectively.This thesis is to designproper synthetic processes which base on the previous literatures and the researchachievements. Through the new synthetic routes, a series of functional β-cyclodextrinderivatives with1,4-substituted-1,2,3-Triazole are prepared. The whole experiment ismade up with four steps, synthesized23compounds,10of which have not beenreported.1. The mono-6-OTs-β-CD was prepared using β-CD as starting material. Afterthe comparison of results in different solvent system, the aqueous system was chosen.The Temperature、reaction time、dosage of Tscl and alkali was the key factor to thereaction. The yield of mono-6-OTs-β-CD was increased after the optimization of thereaction fators.2. The mono-6-N₃-β-CD was prepared through nucleophilic substitution usingthe mono-6-OT_s-β-CD as intermediate. During the separation of mono-6-N₃-β-CD,the recrystallization in water was chosen to replace the traditional column chromatography in order to remove the unreacted sodium azide.3. The phenyl propargyl ether derivatives was prepared using phenol classderivatives and bromination calkynyl as starting material under alkalic conditions.4. Ten novel compounds of β-cyclodextrin derivatives with1,4-substituted-1,2,3-Triazoles were synthesized through the Cu（I）-catalyzed Huisgen1,3-dipolarcycloaddition reaction at60℃using Copper Sulfate Pentahydrate/sodium ascorbateas the catalyst, THF-H₂O （1:1v/v） as the solvent and the structures of the compoundswere determined by IR,1H-NMR and ESI-MS.