Synthesis of 1-β-D-arabinofuranosylcytosine

Synthesis of Oligoribonucleotides Containing 4‐Thiouridine Using the Convertible Nucleoside Approach and the 1‐(2‐Fluorophenyl)‐4‐Methoxypiperidin‐4‐yl Group

“…[20] Reaction with Sodium Hydrogen Sulfide 2',3',5'-O-Triacetyl-4-(1,2,4-triazolyl)uridine (0.24 mmol) was treated with 148.2 mg (2 mmol) of sodium hydrogensulfide in 10 ml DMF. After one day of magnetic stirring at room temperature conversion to 2',3',5'-triacetyl thiouridine was judged to be around 50% by TLC (10% CH 3 OH in CH 2 Cl 2 , starting material Rf = 0.7 fluorescent, final product Rf = 0.8 non fluorescent).…”

Treatment of leukemia L1210 and P388 by arabinosylcytosine‐polysaccharide conjugates

“…AraC was prepared according to literature (BrokeS and Beranek, 1974). Polysaccharide-araC conjugates with PGA and CMG (PGA-araC and CMG-araC) were synthesized according to our previous work (KCry et al, 1990).…”

Synthesis and Reaction of Pyrimidine Nucleosides

“…The debenzoylation of (147) gave 4-thiouridine, which was then converted to various cytidine derivatives (148). (358) By this procedure, thymidine, (358) 5-fluorouridine and its 2' -deoxy and arabino derivatives, (359.360) 2' -amino-2' -deoxy-5fluorouridine, (361) and arabinofuranosyluracil (362) were converted to the respective cytidine derivatives. In the substitution of 4-thiothymidine with dimethyl(or diethyl)-amine the ~-dialkylamino derivatives were obtained in very poor yields.…”

“…(400) Treatment of tri-O-acetyluridine or tri-O-acetylarabinosyluracil with thionyI chloride and dimethylformamide followed by ammonia also gave the ribosyl or arabinosyl cytosines. (401) This thionyl chloride conversion was an adaptation of the established method for converting 6-azauridine to 6-azacytidine. (402) The one-pot conversion of uridine to cytidine was accomplished by simultaneous protection of the sugar hydroxyl groups and activation of the C-4 by trimethylsilylation, followed by ammonolysis with various amines such as pyrrolidine, morpholine, aniline, dimethylaminoethylamine, and hydroxylamine (166), which was then converted to the cytidine derivatives (167) by ammonolysis with various amines including morpholine and aniline.…”