Příprava monosubstituovaných cyklodextrinů selektivní deacetylací
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Tato bakalářská práce se zabývá syntézou monosubstituovaných derivátů cyklodextrinů (CD) pomocí regioselektivní deacetylace.Pro optimalizování přípravy derivátů byly nejprve provedeny pilotní studie, kde byly výtěžky sledovány pomocí vysokoúčinné kapalinové chromatografie (HPLC). Vybraná činidla byla použita pro deacetylaci per-O-acetyl-beta-CD ve větším měřítku, a takto byly získány dva monosubstituované deriváty. Jedná se o per-O-acetyl-2A-hydroxy-beta-CD a per-O-acetyl-6A-hydroxy-beta-CD. Výsledné produkty byly charakterizovány pomocí nukleární magnetické rezonance (NMR) a hmotnostní spektrometrie (MS). Příprava prvně jmenovaného derivátu nebyla doposud publikována.Úvod literární rešerše je zaměřen na historii, strukturu, vlastnosti, výrobu a využití cyklodextrinů v praxi. Ve druhé části jsou stručně shrnuty metody selektivního odchraňování persubstituovaných CD a poslední kapitola se věnuje teorii selektivní deacetylace.
This bachelor thesis deals with synthesis of monosubstituted cyclodextrin (CD) derivatives by regioselective deacetylation.At first, preliminary study was done for optimization of the derivatives preparation. The reaction was monitored by high performance liquid chromatography (HPLC) and the most promising reagents were used for deacetylation of per-O-acetyl-beta-CD on a larger scale. The reactions furnished two monosubstituted derivatives: per-O-acetyl-2A-hydroxy-beta-CD and per-O-acetyl-6A-hydroxy-beta-CD. The products were characterized by nuclear magnetic resonance (NMR) and mass spectrometry (MS). The preparation of the first derivative has not been published yet.The introduction is focused on the history, structure, properties, production and the use of cyclodextrins. In the second part, methods for selective deprotection of persubstituted CDs are briefly summarized and the next chapter deals with the selective deacetylation.
This bachelor thesis deals with synthesis of monosubstituted cyclodextrin (CD) derivatives by regioselective deacetylation.At first, preliminary study was done for optimization of the derivatives preparation. The reaction was monitored by high performance liquid chromatography (HPLC) and the most promising reagents were used for deacetylation of per-O-acetyl-beta-CD on a larger scale. The reactions furnished two monosubstituted derivatives: per-O-acetyl-2A-hydroxy-beta-CD and per-O-acetyl-6A-hydroxy-beta-CD. The products were characterized by nuclear magnetic resonance (NMR) and mass spectrometry (MS). The preparation of the first derivative has not been published yet.The introduction is focused on the history, structure, properties, production and the use of cyclodextrins. In the second part, methods for selective deprotection of persubstituted CDs are briefly summarized and the next chapter deals with the selective deacetylation.
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cyklodextriny, monosubstituovaný derivát, selektivní deacetylace, cyclodextrins, monosubstituted derivative, selective deacetylation