Title of article :
Synthesis of C2 -β -Fluoro-Substituted Adenine Nucleosides Via Pivaloyl Derivatives of Adenosine and 3 -Deoxyadenosine
Author/Authors :
Sivets, Grigorii G. National Academy of Sciences - Institute of Bioorganic Chemistry, Belarus , Kalinichenko, Elena N. National Academy of Sciences - Institute of Bioorganic Chemistry, Belarus , Mikhailopulo, Igor A. National Academy of Sciences - Institute of Bioorganic Chemistry, Belarus , Mikhailopulo, Igor A. University of Kuopio - Department of Pharmaceutical Chemistry, Finland
Abstract :
Syntheses of 9-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)adenine (9) its 3’-deoxy derivative, 9-(2,3-dideoxy-2-fluoro-b-D-threo-pentofuranosyl)adenine (16), with the DAST treatment of the corresponding 3’,5’-di-O-pivaloyladenosine (7) and its 3’-deoxy derivative 14 are described. The role of the pentofuranose ringstereochemistry of nucleosides 7 and 14 in the DAST fluorination is discussed. Stereochemistry of compounds7 and 14 as well as fluorides 9 and 16 was studied by the PSEUROT 6.3 program.
Keywords :
Nucleosides , purine , 2’ , deoxyfluoro derivatives , PSEUROT analysis
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
