83866-20-0Relevant articles and documents
Synthesis of 5-phenylcytosine nucleoside derivatives
Krecmerova, Marcela,Hrebabecky, Hubert,Holy, Antonin
, p. 645 - 655 (2007/10/03)
Reaction of silylated 5-phenylcytosine with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose, catalyzed with tin tetrachloride, and subsequent methanolysis afforded 5-phenylcytidine (2). This compound reacted with thionyl chloride in acetonitrile to give cyclic sulfite 3 which on heating in dimethylformamide was converted into 2,2′-anhydro-1-(β-D-arabinofuranosyl)-5-phenylcytosine (4). Analogous reaction of compound 2 with thionyl chloride at reflux gave 5′-chloro-5′-deoxy-2′,3′-cyclic sulfite 5. Its heating in dimethylformamide afforded 5′-chloro-2,2′-anhydro derivative 6, mild alkaline hydrolysis led to 5′-chloro-5′-deoxy-5-phenylcytidine (7). Alkaline hydrolysis of 5-phenyl-2,2′-anhydrocytidine (4) gave 5-phenylcytosine arabinoside 8, whereas the 2,2′-anhydro derivative 6 afforded 1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)-5-phenylcytosine (11). At higher temperature, the final reaction product was 2,5′-anhydro-5-phenylcytidine(12). 5′-Chloro-5′-deoxynucleosides 7 and 11 reacted with tri-n-butyl-stannane to give 5′-deoxyribofuranosyl and 5′-deoxyarabinofuranosyl derivatives 15 and 16. 5-Phenylcytidine (2) was converted into the N4-acetate 17 with acetic anhydride. Further reaction with acetic anhydride and hydrogen bromide in acetic acid afforded a mixture of peracetylated 2′-bromo and 3′-bromo derivatives 18 and 19. Reaction with Zn/Cu couple gave 5′-O-acetyl-5-phenyl-2′,3′-didehydro derivative 20 and 2′,3′,5′-tri-O-acetyl-5-phenylcytidine (21). Compound 20 was deblocked to 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-phenylcytosine (22). Catalytic hydrogenation of compound 20 over palladium and subsequent deblocking of the protected 2′,3′-dideoxy derivative 23 gave 1-(2, 3-dideoxy-β-D-glycero-pentofuranosyl)-5-phenylcytosine (24).
