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Synthese von 7-Desazainosin durch Phasentransferglycosidierung (1980)

Seela, Frank ; Hasselmann, Doris

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 3389-3393

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ISSN: 0009-2940

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Synthesis of 7-Deazainosine by Phase Transfer GlycosidationPhase transfer glycosidation of 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (2) with 2,3,5-tri-O-benzyl-1-bromo-D-ribose (3) leads to selective N-7 ribosidation giving a mixture of the anomers 4/5. They are separated chromatographically and the anomeric configuration is assigned by 1H and 13C NMR spectroscopy. The protecting groups of 5 were removed by hydrolysis (methyl ether), desulfurisation (methylthio residue) and catalytic hydrogenation (benzyl ether) yielding 7-(ß-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-4(3H)-one (1), the 7-deaza derivative of inosine.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19801131031

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