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Studies toward synthesis of mono-glycosylated dipyrromethanes and analogues of the anti-cancer natural product tolyporphin

The tolyporphin A structure contains a tetrapyrrolic bacteriochlorin macrocycle and also consists of two glycosyl groups directly connected to the pyrroles. In this thesis, 3-glycosylated pyrrole was reacted with Eschenmoser's salt to produce N,N-dimethylamino methylated derivative in 95 % yield. Then, the product was reacted with pyrrole under microwave irradiation to produce glycosylated dipyrromethane in 44 % yield. Mono-glycosylated porphyrin was formed by reacting glycosylated dipyrromethane with 1,9-bis (imino)-5-phenyl dipyrromethane under the standard procedure, 1H NMR was used to confirm the new products.

Identiferoai:union.ndltd.org:UPSALLA1/oai:DiVA.org:uu-307951
Date January 2016
CreatorsAl-Smadi, Derar
PublisherUppsala universitet, Organisk kemi
Source SetsDiVA Archive at Upsalla University
LanguageEnglish
Detected LanguageEnglish
TypeLicentiate thesis, monograph, info:eu-repo/semantics/masterThesis, text
Formatapplication/pdf
Rightsinfo:eu-repo/semantics/openAccess

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