Process for producing 2'-substituted-D-ribofuranosyl purine compounds

US4145531A · kind A · utility

Assignee

• Max-Planck-Gesellschaft zur Föderung der Wissenschaften e.V. · US

Inventors

• Fritz Eckstein · Göttingen, DE
• John Hobbs · Göttingen, DE

Key dates

• Filing date: Apr 28, 1977
• Grant date: Mar 20, 1979
• Expiry date: Apr 28, 1997

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/20
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

2'-Substituted-D-ribofuranosyl purine compounds, especially 2'-azido-D-riuranosyl purine compounds, of the formula ##STR1## in which R.sub.1 is azide, amino, halogen or alkoxy, and PA1 R.sub.2 is the residue of a purine base and particularly a 9-adenyl group, a 7-guanyl group, or a 9-guanyl group (the waved lines in formula I above show that R.sub.2 can be bound in the .alpha.- or .beta.-configuration), Are prepared by a process comprising PA1 (a) reacting a uridine derivative with an alkali azide (when R.sub.1 is to be azide or, through further conversion, an amine group) or a halide (when R.sub.1 is halogen) or with an alkylating agent (when R.sub.1 is alkoxy); PA1 (b) transforming the resulting compound with hydrazine into the corresponding 2-deoxy-ribose; PA1 (c) converting the 2-deoxy-ribose into a 1-O-methylglucoside with methanol in the presence of a strong acid; PA1 (d) reacting the glucoside with acetic anhydride in a polar organic solvent to form a 1-O-methyl-ribose-3,5-diacetate; PA1 (e) converting the diacetate with acetic anhydride in glacial acetic acid, in the presence of a strong acid into a ribose-1,3,5-triacetate; PA1 (f) condensing the triacetate obtained with a …