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- W2079171468 abstract "ara-7-Desazanebularin (2b) und sein 6-Methylthio-Derivat 2a wurden mittels Phasentransferglycosylierung von 4-Methylthio-7H-pyrrolo[2,3-d]pyrimidin (4a) mit 1-Brom-2,3,5-tri-O-benzyl-D-arabinofuranose (7) dargestellt. In Abwesenheit der Halogenose entstehen aus 4a oder 4b in Dichlormethan die N-7-methylenverbruckten Bis-Chromophore 6a bzw. 6b. Im Gegensatz zu 2,4-disubstituierten Pyrrolo[2,3,-d]pyrimidinen wird 4a nicht nur an N-7 sondern auch an N-1 glycosyliert. Anomeren- wie Isomerenanteil lassen sich durch den Phasentransferkatalysator beeinflussen. Die N-1-glycosylierte Verbindung 10 ist im Vergleich zum N-7-Isomer 8a an der N-glycosylischen Bindung hydrolyselabil. Bortrichlorid debenzyliert 8a bzw. 9a zu den anomeren Methylthionucleosiden 2a und 9b. Durch Raney-Nickel-Desulfurierung wird die Titelverbindung 2b erhalten, die intensiv fluoresziert.are-7-Deazanebularine - Synthesis of a Fluorescent Pyrrolo[2,3-d]pyrimidine Nucleoside by Phase-Transfer Glycosylationara-7-Deazanebularine (2b) and its 6-methylthio derivative 2a have been synthesized via phase-transfer glycosylation of 4-methylthio-7H-pyrrolo[2,3-d]pyrimidine (4a) with 1-bromo-2,3,5-tri-O-benzyl-D-arabinofuranose (7). Omitting the halogenose and carrying out the reaction of 4a or 4b in dichloromethane leads to the methylene-bridged chromophores 6a and 6b, respectively. In contrast to pyrrolo[2,3-d]pyrimidines with substituents in position 2 and 4 compound 4a is glycosylated at N-7 and N-1. The formation of anomers and isomers is influenced by the phase-transfer catalyst. The N-1-glycosylated 10 is sensitive against hydrolysis at the N-glycosylic bond which is not found for the N-7 isomer 8a. Debenzylation of the methylthio nucleosides 8a or 9a is accomplished using boron trichloride. Raney nickel catalyst removes the sulfur yielding the title compound 2b which exhibits strong fluorescence." @default.
- W2079171468 created "2016-06-24" @default.
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- W2079171468 date "1983-09-15" @default.
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- W2079171468 title "ara-7-Desazanebularin – Synthese eines fluoreszierenden Pyrrolo[2,3-d]pyrimidin-Nucleosids durch Phasentransferglycosylierung" @default.
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- W2079171468 doi "https://doi.org/10.1002/jlac.198319830913" @default.
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