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Studies toward synthesis of mono-glycosylated dipyrromethanes and analogues of the anti-cancer natural product tolyporphin
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. (Mikael Widersten)ORCID iD: 0000-0003-4603-4540
2016 (English)Licentiate thesis, monograph (Other academic)
Abstract [en]

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. 

Place, publisher, year, edition, pages
Uppsala University, 2016. , p. 44
Keyword [en]
Eschenmoser salt, dipyrromethane, porphyrin.
National Category
Chemical Sciences
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-307951OAI: oai:DiVA.org:uu-307951DiVA, id: diva2:1049118
Presentation
2016-12-12, BMC- C8:301, Husargatan 3, 75123 Uppsala, Uppsala, 13:15 (English)
Opponent
Supervisors
Available from: 2016-12-21 Created: 2016-11-23 Last updated: 2016-12-21Bibliographically approved

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CiteExportLink to record
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