Introduction of a benzyl group onto the 2'-OH of 6-chloropurine 3'-O-benzoylriboside.
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.
Kozai
Shigetada
S
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, Japan.
Fuzikawa
Tomoyo
T
Harumoto
Keisuke
K
Maruyama
Tokumi
T
D000241:Adenosine; D019905:Benzyl Alcohol; D001593:Benzyl Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
C479238:6-chloropurine 3'-O-benzoylriboside; D001593:Benzyl Compounds; D007202:Indicators and Reagents; D011684:Purine Nucleosides; C024008:6-chloropurine riboside; D000241:Adenosine; D019905:Benzyl Alcohol