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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Cytidine is a non-essential aminoacid.
Synonyms: Cytosine β-D-riboside; Cytosine-1-β-D-ribofuranoside; NSC 20258
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 65-46-3 |
Formula : | C9H13N3O5 |
M.W : | 243.22 |
SMILES Code : | OC[C@@H]1[C@H]([C@H]([C@H](N2C(N=C(C=C2)N)=O)O1)O)O |
Synonyms : |
Cytosine β-D-riboside; Cytosine-1-β-D-ribofuranoside; NSC 20258
|
MDL No. : | MFCD00006545 |
InChI Key : | UHDGCWIWMRVCDJ-XVFCMESISA-N |
Pubchem ID : | 6175 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation 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 (85.1%) desiredproduct 5-iodocytidine (191). |
85.1% | With iodine; iodic acid; In tetrachloromethane; water; acetic acid; at 40℃; for 6h; | 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 %) 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 %) 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 72.4% yield. |
51% | With iodine; iodic acid; acetic acid; In tetrachloromethane; water; at 40℃; for 2h; | 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 (0-30%) to give the product 3a,b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.7% | With [1,3]-dioxolan-2-one; In N,N-dimethyl-formamide; at 82.0℃; for 2.0h; | Add 100g cytidine and 500ml N to the three-neck bottle.N-dimethylformamide,After stirring and dispersing evenly,Add 410g of ethylene carbonate,Turn on heating,Warming up to 82 C,After basic dissolution,start the timer,Reaction 2h; TLC showed that the starting material reaction was complete,Stop heating,Naturally cool and stir,When cooling to 40 C,Drop 200ml of methanol,After the addition is completed,Stir at room temperature for 1.2 h,Then the solvent was distilled off under reduced pressure; 2500 ml of methanol was added to the basic evaporation.Beating at room temperature for 3 hours,Filter under reduced pressure,Rinse twice with ethyl acetate,The amount of ethyl acetate used is 200ml each time.The filter cake was dried under vacuum at 65 C for 4 h; the gray solid powder was obtained.Weighing 51.4g,The yield is 47.7%.Based on cytidine,The purity is 79%. |
Tags: Cytidine | Cytosine β-D-riboside | Cytosine-1-β-D-ribofuranoside | Nucleoside Antimetabolite/Analog | Endogenous Metabolite | uridine | RNA | nucleoside | ribofuranose | 65-46-3
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