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- W1589344673 abstract "2,3′-Anhydro-1-(2-desoxy-β-D-xylofuranosyl)-thymin (4) liefert mit HF bzw. HCl in Dioxan die cytostatisch wirksamen Verbindungen 3′-Fluor- bzw. 3′-Chlor-3′-desoxy-thymidin (3 bzw. 7). AlF3 katalysiert die Reaktion zu 3. 3′-O-Mesyl-thymidin (1) reagiert mit Fluoriden nicht zum 1-(2,3-Didesoxy-3-fluor-β-D-xylofuranosyl)-thymin (2), sondem primär zu 4 und dieses zum Teil weiter zu 3. Die Konfiguration an C-3′ von 3 und 7 wird durch Recyclisierung zu 4 bewiesen. Der Cotton-Effekt von 3 und 7 um 270 nm ist positiv. Im alkalischen Milieu gehen 3 und 7 leicht in 3-́Desoxy-2′3′-didehydrothymidin (6) über. Die Säurebeständigkeit nimmt in der Reihenfolge 1-(2-Desoxy-β-D-xylofuranosyl)-thymin (8), Thymidin, 3 und 7 zu. 2,3′-Anhydro-1-(2-deoxy-β-D-xylofuranosyl)thymine (4) reacts with HF or HCl to give compounds with cytostatic activity, namely 3′-fluoro- or 3′-chloro-3′-deoxythymidine (3 or 7). The formation of 3 is catalysed by AlF3 3−O-Mesylthymidine reacts with fluorides to form 4 and in part finally 3, but not 1-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)thymine (2). The configuration at C-3′ of 3 and 7 is established by recyclisation to 4. In alkaline medium, 3 and 7 are easily converted into 2′,3′-didehydro-3′-deoxythymidine (6). 3 and 7 show a positive Cotton effect at 270 nm. The acid resistance increases in the order 1-(2-deoxy-β-D-xylofuranosyl)thymine (8). thymidine. 3 and 7." @default.
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- W1589344673 date "1971-01-01" @default.
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- W1589344673 title "Nucleoside von fluorzuckern- VI" @default.
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