Synthesis of Cyclobutane Nucleosides 2-Preparation of Thymine and Uracil Analogues

Autor:	Abdelaziz Ebead, Edward Lee-Ruff, Joseph Pignatelli, Hanan Afifi
Rok vydání:	2015
Předmět:	Nucleosides Stereoisomerism Uracil Chemistry Techniques Synthetic General Medicine Methoxide Photochemical Processes Borohydride Biochemistry Medicinal chemistry Thymine Cyclobutane chemistry.chemical_compound chemistry Genetics Molecular Medicine Organic chemistry Nucleoside Cyclobutanes Cis–trans isomerism
Zdroj:	Nucleosides, Nucleotides and Nucleic Acids. 34:786-798
ISSN:	1532-2335 1525-7770
DOI:	10.1080/15257770.2015.1075551
Popis:	1-(2-Oxocyclobutyl-4-benzoyloxymethyl)-2,4(1H,3H)-pyrimidinedione and 1-(2-oxocyclobutyl-4-benzoyloxymethyl)-5-methyl-2,4(1H,3H)-pyrimidinedione can be prepared by reaction of uracil and thymine, respectively, with 3-benzoyloxymethyl-2-bromocyclobutanone. The N-alkylation gave both cis and trans isomers with the trans isomer predominating for uracil whereas the trans isomer was the only product which could be isolated for thymine. Both series were subjected to borohydride reduction followed by transesterification with methoxide giving the corresponding uracil and thymine nucleoside analogues. The uracil derivative 1-(2-oxocyclobutyl-4-benzoyloxymethyl)-2,4(1H,3H)-pyrimidinedione was irradiated in aqueous acetonitrile to generate isonucleoside analogues.
Databáze:	OpenAIRE
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