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Preparation of organocatalysts derived from thiourea containing saccharide units
Řehůřková, Tereza ; Veselý, Jan (advisor) ; Smrček, Stanislav (referee)
4 ABSTRACT This diploma thesis is focused on the synthesis of new bifunctional thiourea organic catalysts containing a carbohydrate moiety, in particular D-glucose with modification on the primary hydroxyl group. The first part of this diploma thesis describes a modification of synthesis of the known bifunctional thiourea catalyst with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose and (1R,2R)-diaminocyclohexane. The second part is dedicated to the synthesis of new bifunctional thiourea catalysts with modification of the carbohydrate moiety. We focused on per-O-acetyl-β-D-glucopyranose derivatives with pefluoroalkyl moiety on the primary hydroxyl group. We examined different ways of the preparation of 6-O-perfluoroalkylated glucose derivatives. These perfluoroalkylated carbohydrate compounds were transformed into corresponding glycosyl isothiocyanates. Those derivatives upon treatment of (1R,2R)-diaminocyklohexane or 3,5- bis(trifluormethyl)aniline afforded new bifunctional thiourea organocatalysts.
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Preparation of organocatalysts derived from thiourea containing saccharide units
Řehůřková, Tereza ; Veselý, Jan (advisor) ; Smrček, Stanislav (referee)
4 ABSTRACT This diploma thesis is focused on the synthesis of new bifunctional thiourea organic catalysts containing a carbohydrate moiety, in particular D-glucose with modification on the primary hydroxyl group. The first part of this diploma thesis describes a modification of synthesis of the known bifunctional thiourea catalyst with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose and (1R,2R)-diaminocyclohexane. The second part is dedicated to the synthesis of new bifunctional thiourea catalysts with modification of the carbohydrate moiety. We focused on per-O-acetyl-β-D-glucopyranose derivatives with pefluoroalkyl moiety on the primary hydroxyl group. We examined different ways of the preparation of 6-O-perfluoroalkylated glucose derivatives. These perfluoroalkylated carbohydrate compounds were transformed into corresponding glycosyl isothiocyanates. Those derivatives upon treatment of (1R,2R)-diaminocyklohexane or 3,5- bis(trifluormethyl)aniline afforded new bifunctional thiourea organocatalysts.
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