102044-80-4Relevant academic research and scientific papers
Syntheses of 2,4-Substituted Homo-C-pyrimidinenucleosides
Renz, Hans,Schlimme, Eckhard
, p. 957 - 966 (2007/10/02)
The synthesis of 6-(D-ribofuranosylmethyl)-4-pyrimidinamine (3) was realized on two routes. - (I) 2,4-Dichloro-6-(chloromethyl)pyrimidine (4) was converted into the phosphorane 5 which was condensed with 2,3-O-isopropylidene-5-O-tritylribose 6 via Wittig reaction to give the homo-C-nucleoside 9.This yielded after monoamination, hydrogenolytic halogen exchange and deprotection the nucleoside 3 and its 2-amino isomer 12. - (II) The 3-oxo-4-(D-ribofuranosyl)butyrate 14 was cyclized with thiourea to give the homo-C-nucleoside 15.Reductive desulfuration of 15 and deprotection led to 16 which has been chlorinated to yield 17 via the O-acetyl derivative of compound 16.Contrary to the 2,4-dichloro derivative 9, the 4-chloro derivative 17 was aminated only when heated with ammonia in a sealed tube to give the β-configurated 3.Radioactive labeling of 3 has been achieved by cyclocondensation of 14 with thiourea.
