Synthesis of 4-Amino-7-oxo-7,8-dihydropteridine N-8-β-D-Ribosides—Structural Analogs of Adenosine

✍ Scribed by Dr. Manfred Ott; Prof. Dr. Wolfgang Pfleiderer

• Publisher: John Wiley and Sons
• Year: 1971
• Tongue: English
• Weight: 180 KB
• Volume: 10
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197109311

✦ Synopsis

can, like the isomeric mixture (23) and (23a), be converted into the free isoxanthopterin N-8-P-~-ribofuranoside (29) by treatment with methoxide. Compound (29) is also obtained when ( 21) is debenzylated catalytically with Pd/H, to (25) and then (25) subsequently debenzoylated.

R20H2CYY OR2 OR2

In the treatment of (21) with methoxide, substitution of the benzyloxy by a methoxy group to form ( 27) takes place at the same time as deacylation. No other anomalous reactions have been observed in conversion of blocked derivatives into free N-8-ribosides ( 26)-( 29). The structure and configuration of the glycosidic linkage in each of the substances were established and confirmed by UV and NMR spectroscopy.