82855-67-2Relevant academic research and scientific papers
REACTION OF 2,2'-ANHYDRO-1-(β-D-ARABINOFURANOSYL)-6-AZAURACIL, 4-CHLOROPYRIMIDINE AND 6-CHLOROPURINE NUCLEOSIDES WITH AMINO ACIDS
Hrebabecky, Hubert,Beranek, Jiri
, p. 2689 - 2697 (2007/10/02)
Reaction of cycloazauridine I with glycine and L-lysine in water at pH 10 afforded the glycine derivative II and the Nε-lysine derivative III, respectively.An identical sample of III was prepared by reaction of Nα-formyl-L-lysine with I followed by deformylation of the formed IV.L-Arginine reacts with I in water to give the Nα-derivative V.Under analogous conditions, 6-chloro-9-β-D-ribofuranosylpurine and L-lysine afford the Nε-derivative X.Reaction with Nα- and Nε-formyl-L-lysine at pH 10 leads to the Nε- and Nα-ribosylpurinyl derivatives XI and XII which are deformylated with hydrochloric acid to compounds X and XIII.Benzyl glycinate reacts with 4-chloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)- and 4-chloro-1-2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)pyrimidin-2(1H)-one in chloroform to give benzyl N-(1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrimidin-2(1H)-on-4-yl)glycinate (VI) and N-(1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)pyrimidin-2(1H)-on-4-yl)glycinate (VIII).Their methanolysis with sodium methoxide afforded the free methyl glycinates VII and IX.The reaction of poly(L-lysine) with I and 6-chloro-9-β-D-ribofuranosylpurine was investigated.
4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(β-D-Arabinofuranosyl)cytosine (Ara-C)
Divakar, K.J.,Reese, Colin B.
, p. 1171 - 1176 (2007/10/02)
Treatment of the acetylated derivative (3b), which was prepared from uridine in 86 percent overall yield, with tri(1H-1,2,4-triazol-1-yl)phosphine oxide gave compound (6a) in high yield, and with 3-nitro-1,2,4-triazole and diphenyl phosphorochloridate it gave compound (6b) in high yield.When the former product (6a) was allowed to react with ammonia, methylamine, dimethylamine, and morpholine at room temperature, and the products further deacetylated if necessary, ara-C (1; R1=R2=H) and its corresponding 4-N-alkyl derivatives (1; R1=H, R2=Me), (1: R1=R2=Me), and 1,R2= -(CH2)2O(CH2)2-> were obtained in very high yields. 4-N-Phenyl-ara-C (1; R1=H, R2=Ph) was obtained in high yield when compound (6a) or (6b) was heated with aniline in pyridine solution and the products then deacetylated.The nitro-compound (6b) was converted into the ara-C derivative (1; R1=H, R2=CH2CO2Me), and the sulphide (7) was obtained following the deacetylation of the products of the reaction between the 1,2,4-triazolyl derivative (6a), toluene-p-thiol, and triethylamine.
