A new method for the synthesis of 2'-O-benzyladenosine using Mitsunobu reaction.
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 used. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, Japan.
Shigetada
S
Kozai
Tomoyo
T
Fuzikawa
Keisuke
K
Harumoto
Tokumi
T
Maruyama
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis; D001592:Benzyl Alcohols / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D008956:Models, Chemical; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000737:chemistry; D013237:Stereoisomerism
C480341:2'-O-benzyladenosine; C479238:6-chloropurine 3'-O-benzoylriboside; D000998:Antiviral Agents; D001592:Benzyl Alcohols; D011684:Purine Nucleosides; D000241:Adenosine