87888-91-3Relevant academic research and scientific papers
PREPARATION OF ISOMERIC 3-AMINOPROPYLAMINO DERIVATIVES OF 9-(RS)-(2,3-DIHYDROXYPROPYL)ADENINE
Holy, Antonin
, p. 1910 - 1921 (2007/10/02)
Treatment of 9-(RS)-(2,3-dihydroxypropyl)adenine (III) with bromine in water afforded the 8-bromo derivative IV which on reaction with acetone was converted into the 1,3-dioxolane derivative VI.Reaction of compound VI with 1,3-diaminopropane, followed by acid hydrolysis, gave 9-(R,S)-(2,3-dihydroxypropyl)-8-(3-aminopropylamino)adenine (VIII).Compound IV reacts with 1,3-diaminopropane under formation of a mixture of compound VIII and isomeric 9-(RS)--8-hydroxyadenines (IX,X). 9-(R,S)-(2,3-Dihydroxypropyl)-8-hydroxyadenine (XVII) was prepared by reaction of compound VI with sodium benzoxide in dimethylformamide and subsequent acid hydrolysis.Its tosylation, followed by reaction of the obtained 3'-O-p-toluenesulfonyl derivative XVIII with 1,3-diaminopropane, furnished also the compound IX.In an analogous way, 9-(RS)-adenine (XXI) was prepared from the 3'-O-p-toluenesulfonyl derivative of compound III (XX).
