5-Iodocytidine

White powder

Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachioride was warmed to 40 CC, and iodine (9.6 g, 75.7 mmol) was added.To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 mm. The reaction mixture was stirred at 40 CC for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane—methanol(15:1 to 10:1 to5:1) asgradienteluents resulting in 19.4g (85.1percent) desiredproduct 5-iodocytidine (191).Synthesis of 5-iodocytidine 1 91 : A mixture of cytidine 190 (15.0 g, 61 .7 mmol) in 225 mL of acetic d and 225 mL of carbon tetrachloride was warmed to 40 °C, and iodine (9.6 g, 75.7 mmol) was added. the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of ter within 10 min. The reaction mixture was stirred at 40 °C for 6 h and stirred at room temperature ernight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated der reduced pressure. The residue was purified by flash chromatography on a silica gel column using hloromethane-methanol (15:1 to 1 0:1 to 5:1 ) as gradient eluents resulting in 1 9.4 g (85.1 percent) desired duct 5-iodocytidine (191 ).Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachloride was warmed to 40 °C, and iodine (9.6 g, 75.7 mmol) was added. To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 min. The reaction mixture was stirred at 40 °C for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol (15:1 to 10:1 to 5:1) as gradient eluents resulting in 19.4 g (85.1 percent) desired product 5-iodocytidine (191).The cytidine (0.66 g, 2.7 mol) was added to the three-necked flask, N-iodosuccinimide (0.60 g, 2.4 mol) and 50 ml of methanol, and the temperature was raised to 40-70 ° C. The reaction was stirred for 6-12 hours.Cooled to room temperature, filtered, added with silica gel and removed by rotary evaporation. The column chromatography gave 0.48 g of a pale yellow solid in 72.4percent yield.General procedure: The suspension of nucleosides 2a, b (19 mmol) in water (5.7 mL) was treated with HIO3(9.7 mmol, 1.7 g), AcOH (15.2 mL) and a solution of iodine (11.22 mmol, 2.85 g) inCCl4 (3.8 mL). The resulting mixture was stirred at 40C for 2 h until the starting materialwas consumed or some by-product was formed (monitored by HPLC). After that, water (20 mL) was added. The reaction mixture was cooled to 4C and filtered. The precipitatewas washed with water (2 £ 10 mL). The combined solutions were diluted withwater (250 ml) and extracted with benzene (3 £ 150 mL). The aqueous layer was evaporatedunder reduced pressure. The product was purified by RPC in a linear gradient ofEtOH in water (0–30percent) to give the product 3a, b.

Molecular Weight:369.11
XLogP3:-1.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:368.98217
Monoisotopic Mass:368.98217
Topological Polar Surface Area:129
Heavy Atom Count:18
Complexity:426
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes