Introduction of a Benzyl Group onto the 2′-OH of 6-Chloropurine 3′-O-Benzoylriboside

• Published in: Nucleosides, nucleotides & nucleic acids Vol. 22; no. 5-8; pp. 779 - 781
• Main Authors: Kozai, Shigetada, Fuzikawa, Tomoyo, Harumoto, Keisuke, Maruyama, Tokumi
• Format: Journal Article
• Language: English
• Published: United States Taylor & Francis Group 01-10-2003
• Subjects: Adenosine; Benzyl Alcohol; Benzyl Compounds - chemistry; Indicators and Reagents; Models, Molecular; Molecular Conformation; Purine Nucleosides - chemical synthesis; Purine Nucleosides - chemistry
• ISSN: 1525-7770; 1532-2335
• DOI: 10.1081/NCN-120022633

A new method to introduce a benzyl group onto the 2′-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3′-O-benzoylriboside and its 5′-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2′-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent. The product was converted to adenosine, indicating that the stereochemistry at C-2′ is retained.