PRODUCTION OF (1S,4R)-OR(1R,4S)-4-(2-AMINO-6-CHLORO9H-PURIN-9-YL)-2-CYCLOPENTENE-1-METHANOL

PROBLEM TO BE SOLVED: To produce the subject compound useful as an intermediate, etc., for producing a 2-aminopurine nucleoside at a low cost by acylating 2- azabicyclo-hept-5-en-3-ones, reducing the resultant compounds and then reacting the obtained product with a specific microorganism, etc. SOLUT...

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Hauptverfasser:	BURGDORF KURT, O'MURCHU COLM DR, ETTER KAY-SARA, DUC LAURENT DR, BRIEDEN WALTER DR, BERNEGGER CHRISTINE DR, BOSSARD PIERRE DR, BIRCH OLWEN MARY DR, BRUX FRANK, GUGGISBERG YVES DR, GORDON JOHN, URBAN EVA-MARIA
Format:	Patent
Sprache:	eng
Schlagworte:	ACYCLIC OR CARBOCYCLIC COMPOUNDS BEER BIOCHEMISTRY CHEMISTRY ENZYMOLOGY FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE HETEROCYCLIC COMPOUNDS METALLURGY MICROBIOLOGY MUTATION OR GENETIC ENGINEERING ORGANIC CHEMISTRY PROCESSES USING MICROORGANISMS SPIRITS VINEGAR WINE
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Zusammenfassung:	PROBLEM TO BE SOLVED: To produce the subject compound useful as an intermediate, etc., for producing a 2-aminopurine nucleoside at a low cost by acylating 2- azabicyclo-hept-5-en-3-ones, reducing the resultant compounds and then reacting the obtained product with a specific microorganism, etc. SOLUTION: A (±)-2-azabicyclo[2.2.1]hept-5-en-3-one represented by formula I is acylated to provide an N-acylated derivative represented by formula II (R is a 1-4C alkyl, a 1-4C alkoxy, an aryl or an aryloxy), which is then reduced to afford a cyclopentene derivative represented by formula III. The resultant cyclopentene derivative represented by formula III is subsequently reacted with a microorganism capable of assimilating the compound as only one nitrogen source, as only one carbon source or as the only one nitrogen source and the only one carbon source or an Nacetylaminoalcohol hydrolase, etc., to provide an optically active amino derivative, which is then reacted with an N-(2- amino-4,6dichloro-5-pyridinyl)formamide represented by formula IV and further cyclized to thereby afford the objective compound represented by formula V.