CYTIDINE
Conditions | Yield |
---|---|
In methanol; water at 50℃; for 36h; Hydrolysis; | 99% |
CYTIDINE
Conditions | Yield |
---|---|
In methanol; water at 50℃; for 26h; Hydrolysis; | 99% |
Conditions | Yield |
---|---|
With sodium methylate; guanidine nitrate In methanol; dichloromethane at 0℃; for 0.166667h; | 95% |
With methanol; water; triethylamine at 71℃; for 0.75h; | 92% |
2',3',5'-tri-O-acetylcytidine
CYTIDINE
Conditions | Yield |
---|---|
With ammonia In dichloromethane at 25℃; | 93% |
With ammonia In methanol at 25℃; for 24h; Yield given; | |
In ammonium hydroxide Yield given; |
CYTIDINE
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 10h; | 89% |
[1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2-nitro-benzyl ester
CYTIDINE
Conditions | Yield |
---|---|
In 1,4-dioxane; water for 1.16667h; UV-irradiation; | 89% |
4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one
CYTIDINE
Conditions | Yield |
---|---|
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction; | 89% |
CYTIDINE
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 105℃; for 3h; | 80.9% |
1-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 4-(O-benzyloxime)
A
uridine 4-oxime
B
CYTIDINE
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 60℃; for 1h; | A 22% B 77% |
CYTIDINE
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide | 76.5% |
Conditions | Yield |
---|---|
Stage #1: 1-(β-D-xylo-pentofuranosyl)cytosine With thionyl chloride In acetonitrile at 25℃; for 5h; Stage #2: With sodium hydrogencarbonate In N,N-dimethyl-formamide at 105℃; for 3h; | 76.5% |
Multi-step reaction with 2 steps 1: SOCl2 / acetonitrile 2: 76.5 percent / NaHCO3 / dimethylformamide View Scheme |
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-octanoylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
CYTIDINE
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol Ambient temperature; | 74% |
2-thiocytidine
A
2,4-diaminopyrimidine
B
cytidine 2′,3′-cyclic monophosphate
C
CYTIDINE
Conditions | Yield |
---|---|
With dihydrogen phosphate; formamide Heating; | A 21% B 24% C 48% |
2-thiocytidine
CYTIDINE
Conditions | Yield |
---|---|
With water In aq. phosphate buffer at 60℃; for 2016h; pH=7; | 41% |
N4-benzoyl-1-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-cytosine
A
N4-benzoylcytidine
B
CYTIDINE
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethylguanidine In methanol; dichloromethane at 20℃; for 0.333333h; | A 40% B n/a |
Conditions | Yield |
---|---|
With water In aq. phosphate buffer at 60℃; for 2016h; pH=5; | A 8% B 33% |
D-Ribose
Cytosine
CYTIDINE
Conditions | Yield |
---|---|
In ethanol; water; acetonitrile at 60 - 70℃; for 192h; | 12% |
5-(chloromercuri)cytidine
N,N'-Bis(trifluoroacetyl)cystamine
A
N-{2-[4-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-ylsulfanyl]-ethyl}-2,2,2-trifluoro-acetamide
B
CYTIDINE
Conditions | Yield |
---|---|
With lithium tetrachloropalladate(II) In methanol Ambient temperature; | A 10.1% B n/a |
Conditions | Yield |
---|---|
With phosphoric acid; magnesium sulfate In water at 20℃; under 760.051 Torr; | 0.7% |
N4-acetyl-O2',O3',O5'-tribenzoyl-cytidine
CYTIDINE
Conditions | Yield |
---|---|
With ethanol; ammonia |
1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil
CYTIDINE
Conditions | Yield |
---|---|
With ethanol; ammonia |
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
N4-octanoylcytosine
CYTIDINE
Conditions | Yield |
---|---|
With methanol; sodium; tin(IV) chloride 1.) 1,2-dichloroethane, 20 h room temperature; 2.) MeOH, reflux 1 h; Yield given. Multistep reaction; |
2-methoxy-1-β-D-ribofuranosyl-pyrimidine-4-one
A
CYTIDINE
B
2-amino-1-(β-D-ribofuranosyl)pyrimidin-4(1H)-one
Conditions | Yield |
---|---|
With ammonia at 20℃; Product distribution; half-time; |
orotate anion
A
2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid anion
B
CYTIDINE
Conditions | Yield |
---|---|
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5; |
Conditions | Yield |
---|---|
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5-8.8; |
cytidine 2′,3′-cyclic monophosphate
A
3'-monophosphate of cytidine
C
CYTIDINE
Conditions | Yield |
---|---|
alpha cyclodextrin In water at 20℃; Rate constant; Mechanism; pH=11.08 (hydrogen bicarbonate buffer); cleavage selectivity; without catalyst, other chemically modified cyclodextrins, other temperature, other additives; |
Conditions | Yield |
---|---|
In water at 20℃; Rate constant; pH 8.5-8.8; |
4-[2-(4-cyanophenyl)ethenyl]-1-methylpyridinium iodide
B
CYTIDINE
Conditions | Yield |
---|---|
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5-8.8; |
B
3'-monophosphate of adenosine
C
CYTIDINE
Conditions | Yield |
---|---|
alpha cyclodextrin at 50℃; Rate constant; pH=11.08; | A 21 % Chromat. B 79 % Chromat. C n/a |
β‐cyclodextrin at 50℃; Rate constant; pH=11.08; | A 88 % Chromat. B 12 % Chromat. C n/a |
cyclomaltooctaose at 50℃; Rate constant; pH=11.08; | A 70 % Chromat. B 30 % Chromat. C n/a |
at 50℃; Rate constant; pH=11.08; | A 52 % Chromat. B 48 % Chromat. C n/a |
Di-tert-butyldichlorosilane
CYTIDINE
3',5'-O-(Di-tert-butylsilanediyl)cytidine
Conditions | Yield |
---|---|
With silver nitrate In N,N-dimethyl-formamide at 0℃; for 0.5h; | 100% |
With silver nitrate DMF; Yield given. Multistep reaction; |
1,1,1,3,3,3-hexamethyl-disilazane
CYTIDINE
O2',O3',O5'-tris-trimethylsilanyl-cytidine
Conditions | Yield |
---|---|
With pyridine In acetonitrile for 2h; Heating; | 100% |
With chloro-trimethyl-silane In acetonitrile at 20℃; for 1h; | |
With ammonium sulfate In 1,4-dioxane Heating; |
tert-butylchlorodiphenylsilane
CYTIDINE
5'-O-(tert-butyldiphenylsilyl)cytidine
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 18h; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 65.2% |
With 1H-imidazole In N,N-dimethyl-formamide for 20h; Ambient temperature; |
Conditions | Yield |
---|---|
With tiolacetic acid In pyridine at 50℃; for 4h; | 100% |
Multi-step reaction with 2 steps 1: 98 percent / sodium acetate / 1 h / 120 °C 2: 77 percent / Aspergillus niger lipase Amano A; phosphate buffer / H2O / 15.5 h / 37 °C / pH 7.0 View Scheme | |
Multi-step reaction with 2 steps 1: pyridine 2: 1-hydroxybenzotriazole / acetonitrile / 17 h / Ambient temperature View Scheme | |
With acetic anhydride In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With pyridine at 80℃; for 1h; | 100% |
With pyridine at 20℃; Cooling with ice; | 99% |
With sodium acetate at 120℃; for 1h; Acetylation; | 98% |
molecular sieve; potassium chloride at 100℃; for 3h; | 86% |
With pyridine at 80℃; for 2h; |
tert-butyldimethylsilyl chloride
CYTIDINE
4-amino-1-((2R,3R,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Conditions | Yield |
---|---|
With pyridine; 1H-imidazole at 20℃; | 100% |
With pyridine; silver nitrate; triethylamine In tetrahydrofuran | 96% |
With 1H-imidazole; triethylsilyl chloride at 20℃; for 48h; Inert atmosphere; | 80% |
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 72h; Inert atmosphere; | |
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 20h; |
O-benzylhydoxylamine hydrochloride
CYTIDINE
N4-(O-(benzyloxy))cytidine
Conditions | Yield |
---|---|
With pyridine at 100℃; | 100% |
With pyridine at 110℃; | |
With pyridine at 80℃; for 12h; |
Di-tert-butyldichlorosilane
tert-butyldimethylsilyl chloride
CYTIDINE
2'-O-(tert-butyldimethylsilyl)-3',5'-O-(di-tert-butylsilylene)cytidine
Conditions | Yield |
---|---|
Stage #1: Di-tert-butyldichlorosilane; CYTIDINE With silver nitrate In N,N-dimethyl-formamide at 4 - 20℃; for 4h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 15h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction; | 99% |
With oxygen; nitrogen(II) oxide In dimethyl sulfoxide for 1h; Ambient temperature; | 47% |
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products; |
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide for 2.4h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide for 2.4h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
at 20℃; for 5h; Condensation; | 99% |
4-methyl-benzoyl chloride
CYTIDINE
4-N-2',3',5'-tri-O-tetra(4-methylbenzoyl)cytidine
Conditions | Yield |
---|---|
With pyridine at 20℃; | 99% |
With pyridine at 20℃; for 3h; |
Conditions | Yield |
---|---|
With lithium perchlorate for 10h; Heating; | 99% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 0.0166667h; Irradiation; | 98% |
In DMF (N,N-dimethyl-formamide) at 20℃; for 20h; | 98.3% |
In N,N-dimethyl-formamide at 20℃; for 20h; | 98.3% |
tert-butyldimethylsilyl chloride
CYTIDINE
5'-O-(tert-butyldimethylsilyl)cytidine
Conditions | Yield |
---|---|
With pyridine; dmap | 98% |
With pyridine; 1H-imidazole at 0 - 20℃; Inert atmosphere; | 97% |
With pyridine; 1H-imidazole at 0 - 20℃; for 12h; Inert atmosphere; | 96% |
CYTIDINE
5'-chloro-5'-deoxy-2',3'-O-sulphinylcytidine hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In acetonitrile for 0.75h; Heating; | 98% |
dichloro-1,4-diazacycloheptaneplatinum(II)
CYTIDINE
Conditions | Yield |
---|---|
With H2O In N,N-dimethyl-formamide byproducts: AgCl; AgNO3 added to soln. of Pt compd., mixt. stirred in dark for 5 d at 45°C, AgCl filtered, org. compd. added to filtrate and stirred for 96h; soln. filtered, concd. in vac., pptd. with acetone, product filtered, washed with CH2Cl2 and acetone, dried in vac.; elem. anal.; | 98% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B In 1,4-dioxane at 60℃; for 43h; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid In acetone at 20℃; Inert atmosphere; | 98% |
With sulfuric acid In acetone at 20℃; for 2h; | 95.25% |
Conditions | Yield |
---|---|
With pyridine at 100℃; | 97% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
CYTIDINE
3',5'-O-[(1,1,3,3-tetraisopropyl)-1,3-disiloxanediyl]cytidine
Conditions | Yield |
---|---|
With pyridine | 96% |
With pyridine | 92% |
With pyridine for 4h; cooling; | 92% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 0.0111111h; Irradiation; | 96% |
In acetonitrile for 3h; Reflux; | 96% |
In N,N-dimethyl-formamide for 0.0111111h; Microwave radiation; | 95% |
Conditions | Yield |
---|---|
With ammonium hydroxide; chloro-trimethyl-silane In pyridine; water; acetone | 96% |
With ammonium hydroxide; chloro-trimethyl-silane In pyridine; water; acetone | 96% |
Stage #1: CYTIDINE With pyridine; chloro-trimethyl-silane at 20℃; for 1.5h; Cooling with ice; Stage #2: benzoyl chloride at 20℃; Cooling with ice; | 95% |
Conditions | Yield |
---|---|
Stage #1: CYTIDINE With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Stage #2: 4-chlorobenzoyl chloride for 2h; Stage #3: With ammonia In water at 0℃; for 0.5h; | 96% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 6h; Cooling with ice; | 95% |
With sulfuric acid at 0 - 20℃; for 12h; | 93% |
Stage #1: acetone; CYTIDINE With perchloric acid at 20℃; for 1.5h; Stage #2: With ammonia In water at 20℃; for 3h; | 74% |
Conditions | Yield |
---|---|
In acetone for 6h; Inert atmosphere; | 95% |
The IUPAC name of Cytidine is 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one. With the CAS registry number 65-46-3, it is also named as 1-beta-D-Ribofuranosylcytosine. The product's categories are Pharmaceutical Intermediates; Fine Chemical & Intermediates; Pyridines, Pyrimidines, Purines and Pteredines; Biochemistry; Nucleosides and their Analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic Acids, and the other registry numbers are 4395-95-3; 494210-74-1; 873077-03-3. Besides, it is white crystalline powder, which should be stored in dark, dry and sealed place at room temperature. It is a component of RNA which is attached to a deoxyribose ring. In addition, this chemical is stable and incompatible with strong oxidizing agents.
Physical properties about Cytidine are: (1)ACD/LogP: -1.808; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.82; (4)ACD/LogD (pH 7.4): -1.81; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 2.39; (8)ACD/KOC (pH 7.4): 2.47; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.756; (13)Molar Refractivity: 52.643 cm3; (14)Molar Volume: 128.433 cm3; (15)Polarizability: 20.869 10-24cm3; (16)Surface Tension: 89.588996887207 dyne/cm; (17)Density: 1.894 g/cm3; (18)Flash Point: 283.816 °C; (19)Enthalpy of Vaporization: 94.8 kJ/mol; (20)Boiling Point: 545.678 °C at 760 mmHg
Preparation of Cytidine: this chemical can be prepared by 1-(2',3',4'-Tri-O-benzoyl-a-D-xylofuranosyl)-4-thiouracil.
This reaction needs Ammonia and Methanol at temperature of 100 °C. The reaction time is 18 hours. The yield is 76 %.
Uses of Cytidine: it is used for biochemical research and organic synthesis. It is also used for producing cytarabine, ring cell, and CTP, cytidine diphosphate choline, etc.
When you are using this chemical, please be cautious about it as the following: it is possible risk of irreversible effects. You should avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1;
(2)InChIKey=UHDGCWIWMRVCDJ-XVFCMESISA-N;
(3)Smilesn1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)cc1)=O
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 2700mg/kg (2700mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Russian Pharmacology and Toxicology Vol. 40, Pg. 66, 1977. |
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