Home Cart 0 Sign in  

[ CAS No. 1147-23-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1147-23-5
Chemical Structure| 1147-23-5
Structure of 1147-23-5 * Storage: {[proInfo.prStorage]}

Quality Control of [ 1147-23-5 ]

Related Doc. of [ 1147-23-5 ]

SDS
Alternatived Products of [ 1147-23-5 ]
Alternatived Products of [ 1147-23-5 ]

Product Details of [ 1147-23-5 ]

CAS No. :1147-23-5 MDL No. :MFCD00056070
Formula : C9H12IN3O5 Boiling Point : 565.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :369.11 g/mol Pubchem ID :159359
Synonyms :

Safety of [ 1147-23-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1147-23-5 ]

  • Upstream synthesis route of [ 1147-23-5 ]
  • Downstream synthetic route of [ 1147-23-5 ]

[ 1147-23-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 65-46-3 ]
  • [ 1147-23-5 ]
YieldReaction ConditionsOperation in experiment
85.1% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 20 - 40℃; 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).
85.1% With iodine; iodic acid In tetrachloromethane; water; acetic acid at 40℃; for 6 h; 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 ).
85.1% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 20 - 40℃; 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).
72.4% With N-iodo-succinimide In methanol at 40 - 70℃; 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.
51% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 40℃; for 2 h; 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.

Reference: [1] Patent: WO2015/196130, 2015, A2, . Location in patent: Page/Page column 634; 635
[2] Patent: WO2015/196128, 2015, A2, . Location in patent: Page/Page column 642
[3] Patent: EP2918275, 2015, A1, . Location in patent: Paragraph 2219; 2220
[4] Patent: EP2918275, 2016, B1, . Location in patent: Paragraph 2219; 2220
[5] Journal of the American Chemical Society, 2015, vol. 137, # 1, p. 34 - 37
[6] Synthesis, 2003, # 7, p. 1039 - 1042
[7] Patent: CN106674316, 2017, A, . Location in patent: Paragraph 0015-0016; 0019-0020
[8] Synthesis, 2009, # 23, p. 3957 - 3962
[9] Tetrahedron Letters, 1999, vol. 40, # 51, p. 8961 - 8964
[10] Organic Preparations and Procedures International, 2018, vol. 50, # 3, p. 332 - 342
[11] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 8, p. 2688 - 2697
Historical Records