65-46-3

Basic information

• Product Name: Cytidine
• Synonyms: 1beta-D-Ribofuranosylcytosine;1-beta-ribofuranosylcytosine;1beta-Ribofuranosylcytosine;2(1H)-Pyrimidinone, 4-amino-1-beta-D-ribofuranosyl-;4-amino-1-beta-d-ribofuranosyl-2(1h)-pyrimidinon;beta-D-Ribofuranoside, cytosine-1;Cyd;Cytidine
• CAS NO: 65-46-3
• Molecular Formula: C₉H₁₃N₃O₅
• Molecular Weight: 243.22
• EINECS: 200-610-9
• Product Categories: Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;nucleoside;Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Pyridines, Pyrimidines, Purines and Pteredines;Inhibitors
• Mol File: 65-46-3.mol
• Article Data: 95

Chemical Properties

• Melting Point: 210-220 °C (dec.)(lit.)
• Boiling Point: 386.09°C (rough estimate)
• Flash Point: 283.8 °C
• Appearance: White to almost white/powder
• Density: 1.3686 (rough estimate)
• Vapor Pressure: 3.5E-14mmHg at 25°C
• Refractive Index: 34 ° (C=0.7, H2O)
• Storage Temp.: Store at RT.
• Solubility: H2O: 50 mg/mL
• PKA: 4.22, 12.5(at 25℃)
• Water Solubility: SOLUBLE
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Protect from moisture.
• Merck: 14,2786
• BRN: 89173
• CAS DataBase Reference: Cytidine(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine(65-46-3)
• EPA Substance Registry System: Cytidine(65-46-3)

Safety Data

• Statements: 68
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: UW7370000
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 65-46-3(Hazardous Substances Data)

Usage

Description

Cytidine is a pyrimidine nucleoside that is composed of the pyrimidine base cytosine attached to the sugar ribose. As a constituent of RNA, cytidine pairs with guanine, and it is a precursor of uridine. Cytidine can incur several modifications in mRNA, including methylation and acetylation, that function to regulate translation. Cytidine can also be formylated to 5-formylcytidine in mitochondrial methionine transfer RNA (tRNAMet).

Chemical Properties

Cytidine is a component of RNA. It is a white water-soluble solid. which is only slightly soluble in ethanol.There are a variety of cytidine analogs with potentially useful pharmacology.

Uses

Cytidine is a nucleoside molecule that is formed when cytosine is attached to a ribose ring, cytidine is a component of RNA. It was isolated from yeast nucleic acid. It can increases cell membrane phospholipids. Cytidine is used to synthesize enzyme inhibitors, antiviral agents, and anticancer agents. And also used as constituent of nucleic acids.

Definition

ChEBI: cytidine is a pyrimidine nucleoside in which cytosine is attached to ribofuranose via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It derives from a cytosine.The derivednucleotides, cytidine mono-, di-, andtriphosphate (CMP, CDP, and CTP respectively)participate in various biochemicalreactions, notably inphospholipid synthesis.

Application

Cytidine has been used as a non-essential aminoacid component of minimal essential medium (MEM) to analyse interspecies somatic cell nucleus transfer (iSCNT)-derived blastocysts. It has also been used as a supplement in the culture medium of HeLa cells, to study the effects of cytidine addition on rods and rings (RR) induced by glutamine deprivation.Cytidine has been used as a component to prepare ribonucleoside stock solution to assess its effects on the anaerobic growth of several Bacillus mojavensis strains.

General Description

White crystalline powder.

Air & Water Reactions

Cytidine is hygroscopic. Water soluble.

Reactivity Profile

Cytidine is incompatible with strong oxidizing agents. . Will react as a weak base.

Fire Hazard

Flash point data for Cytidine are not available; however, Cytidine is probably combustible.

Purification Methods

Cytidine crystallises from 90% aqueous EtOH. It has also been converted to sulfate by dissolving (~200mg) in a solution of EtOH (10mL) containing H2SO4 (50mg), whereby the salt crystallises out. It is collected, washed with EtOH and dried for 5hours at 120o/0.1mm. The sulfate has m 225o. The free base is obtained by shaking the salt solution with a weak ion-exchange resin, filtering, evaporating and recrystallising the residue from EtOH as before. [Fox & Goodman J Am Chem Soc 73 3256 1956, Fox & Shugar Biochim Biophys Acta 9 369 1952; see Prytsas & Sorm in Synthetic Procedures in Nucleic Acid Chemistry (Zorbach & Tipson Eds) Vol 1 404 1973.] [Beilstein 25 III/IV 3667.]

InChI:InChI=1/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

Synthetic route

4N-dimethylaminomethylene cytidine → CYTIDINE (65-46-3)

Conditions	Yield
In methanol; water at 50℃; for 36h; Hydrolysis;	99%

4N-dibenzylaminomethylene cytidine → CYTIDINE (65-46-3)

Conditions	Yield
In methanol; water at 50℃; for 26h; Hydrolysis;	99%

4-N-2',3',5'-O-tetraacetylcytidine (5040-18-6) → CYTIDINE (65-46-3)

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 (56787-28-1) → CYTIDINE (65-46-3)

Conditions	Yield
With ammonia In dichloromethane at 25℃;	93%
With ammonia In methanol at 25℃; for 24h; Yield given;
In ammonium hydroxide Yield given;

6-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6H-tetrazolo[1,5-c]pyrimidin-5-one → CYTIDINE (65-46-3)

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 (473910-24-6) → CYTIDINE (65-46-3)

Conditions	Yield
In 1,4-dioxane; water for 1.16667h; UV-irradiation;	89%

4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one (10578-79-7) → CYTIDINE (65-46-3)

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%

2,2'-anhydrocytidine hydrochloride → CYTIDINE (65-46-3)

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) (800379-05-9) → uridine 4-oxime (3258-02-4) + CYTIDINE (65-46-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 60℃; for 1h;	A 22% B 77%

4-Amino-1-((4aR,6R,7R,7aR)-7-hydroxy-2-oxo-tetrahydro-2λ4-furo[3,2-d][1,3,2]dioxathiin-6-yl)-1H-pyrimidin-2-one → CYTIDINE (65-46-3)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide	76.5%

1-(β-D-xylo-pentofuranosyl)cytosine (3530-56-1) → CYTIDINE (65-46-3)

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 (97627-00-4) → CYTIDINE (65-46-3)

Conditions	Yield
With sodium hydroxide In ethanol Ambient temperature;	74%

2-thiocytidine (13233-20-0, 13239-97-9) → 2,4-diaminopyrimidine (156-81-0) + cytidine 2′,3′-cyclic monophosphate (50574-59-9) + CYTIDINE (65-46-3)

Conditions	Yield
With dihydrogen phosphate; formamide Heating;	A 21% B 24% C 48%

2-thiocytidine (13233-20-0, 13239-97-9) → CYTIDINE (65-46-3)

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 (97626-95-4) → N4-benzoylcytidine (13089-48-0) + CYTIDINE (65-46-3)

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In methanol; dichloromethane at 20℃; for 0.333333h;	A 40% B n/a

2-thiocytidine (13233-20-0, 13239-97-9) → 2-thiouridine (20235-78-3) + CYTIDINE (65-46-3)

Conditions	Yield
With water In aq. phosphate buffer at 60℃; for 2016h; pH=5;	A 8% B 33%

D-Ribose (532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7) + Cytosine (71-30-7) → CYTIDINE (65-46-3)

Conditions	Yield
In ethanol; water; acetonitrile at 60 - 70℃; for 192h;	12%

5-(chloromercuri)cytidine (65523-07-1) + N,N'-Bis(trifluoroacetyl)cystamine (118042-46-9) → 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 (135638-75-4) + CYTIDINE (65-46-3)

Conditions	Yield
With lithium tetrachloropalladate(II) In methanol Ambient temperature;	A 10.1% B n/a

β-D-ribofuranose (36468-53-8) + Cytosine (71-30-7) → CYTIDINE (65-46-3)

Conditions	Yield
With phosphoric acid; magnesium sulfate In water at 20℃; under 760.051 Torr;	0.7%

N4-acetyl-O2',O3',O5'-tribenzoyl-cytidine (27391-03-3) → CYTIDINE (65-46-3)

Conditions	Yield
With ethanol; ammonia

1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil (15049-50-0) → CYTIDINE (65-46-3)

Conditions	Yield
With ethanol; ammonia

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + N4-octanoylcytosine (33304-87-9) → CYTIDINE (65-46-3)

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 (53337-88-5) → CYTIDINE (65-46-3) + 2-amino-1-(β-D-ribofuranosyl)pyrimidin-4(1H)-one (489-59-8)

Conditions	Yield
With ammonia at 20℃; Product distribution; half-time;

orotate anion (73-97-2) + C9H13N3O5(1-) → 2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid anion (73-97-2) + CYTIDINE (65-46-3)

Conditions	Yield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5;

1-methyl-4-carboxypyridinium chloride (5746-18-9) + C9H13N3O5(1-) → C7H8NO2 (36455-39-7) + CYTIDINE (65-46-3)

Conditions	Yield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5-8.8;

cytidine 2′,3′-cyclic monophosphate (50574-59-9) → 3'-monophosphate of cytidine (47136-83-4) + 2'-monophosphate of cytidine + CYTIDINE (65-46-3)

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;

N-methyl-4-methylpyridinium iodide (2301-80-6) + C9H13N3O5(1-) → 1,4-dimethylpyridinyl radical + CYTIDINE (65-46-3)

Conditions	Yield
In water at 20℃; Rate constant; pH 8.5-8.8;

4-[2-(4-cyanophenyl)ethenyl]-1-methylpyridinium iodide (26467-87-8) + C9H13N3O5(1-) → C15H13N2 + CYTIDINE (65-46-3)

Conditions	Yield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5-8.8;

C19H24N8O11P(1-) → 2'-monophosphate of adenosine + 3'-monophosphate of adenosine (135245-29-3) + CYTIDINE (65-46-3)

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 (18395-90-9) + CYTIDINE (65-46-3) → 3',5'-O-(Di-tert-butylsilanediyl)cytidine (126628-28-2)

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 (999-97-3) + CYTIDINE (65-46-3) → O2',O3',O5'-tris-trimethylsilanyl-cytidine (51432-41-8)

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 (58479-61-1) + CYTIDINE (65-46-3) → 5'-O-(tert-butyldiphenylsilyl)cytidine (58479-65-5)

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;

CYTIDINE (65-46-3) → N-acetylcytidine (3768-18-1)

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

acetic anhydride (108-24-7) + CYTIDINE (65-46-3) → 4-N-2',3',5'-O-tetraacetylcytidine (5040-18-6)

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 (18162-48-6) + CYTIDINE (65-46-3) → 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 (72409-19-9)

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 (2687-43-6) + CYTIDINE (65-46-3) → N4-(O-(benzyloxy))cytidine (800379-05-9)

Conditions	Yield
With pyridine at 100℃;	100%
With pyridine at 110℃;
With pyridine at 80℃; for 12h;

Di-tert-butyldichlorosilane (18395-90-9) + tert-butyldimethylsilyl chloride (18162-48-6) + CYTIDINE (65-46-3) → 2'-O-(tert-butyldimethylsilyl)-3',5'-O-(di-tert-butylsilylene)cytidine (438582-96-8)

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%

CYTIDINE (65-46-3) → uridine (58-96-8)

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;

iodomethane-d3 (865-50-9) + CYTIDINE (65-46-3) → C10H13(2)H3N3O5(1+)*I(1-)

Conditions	Yield
In N,N-dimethyl acetamide for 2.4h; Ambient temperature;	99%

CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 6-Amino-3-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methyl-2-oxo-2,3-dihydro-pyrimidin-1-ium; iodide

Conditions	Yield
In N,N-dimethyl acetamide for 2.4h; Ambient temperature;	99%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + CYTIDINE (65-46-3) → 4N-dimethylaminomethylene cytidine

Conditions	Yield
at 20℃; for 5h; Condensation;	99%

4-methyl-benzoyl chloride (874-60-2) + CYTIDINE (65-46-3) → 4-N-2',3',5'-tri-O-tetra(4-methylbenzoyl)cytidine (863592-01-2)

Conditions	Yield
With pyridine at 20℃;	99%
With pyridine at 20℃; for 3h;

acetic anhydride (108-24-7) + CYTIDINE (65-46-3) → 2,3,5-O-acetyl-N-acetylcytidine

Conditions	Yield
With lithium perchlorate for 10h; Heating;	99%

benzoic acid anhydride (93-97-0) + CYTIDINE (65-46-3) → N4-benzoylcytidine (13089-48-0)

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 (18162-48-6) + CYTIDINE (65-46-3) → 5'-O-(tert-butyldimethylsilyl)cytidine (72409-16-6, 82976-97-4)

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 (65-46-3) → 5'-chloro-5'-deoxy-2',3'-O-sulphinylcytidine hydrochloride (69260-61-3)

Conditions	Yield
With thionyl chloride In acetonitrile for 0.75h; Heating;	98%

dichloro-1,4-diazacycloheptaneplatinum(II) (154068-67-4) + silver nitrate + CYTIDINE (65-46-3) → [Pt(II)(homopiperazine)(cytidine)2](NO3)2

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%

2-acetone-isobutyryl oxime (138421-23-5) + CYTIDINE (65-46-3) → 5'-O-isobutyrylcytidine

Conditions	Yield
With Candida antarctica lipase B In 1,4-dioxane at 60℃; for 43h;	98%

2,2-dimethoxy-propane (77-76-9) + CYTIDINE (65-46-3) → C12H17N3O5*H2O4S

Conditions	Yield
With sulfuric acid In acetone at 20℃; Inert atmosphere;	98%
With sulfuric acid In acetone at 20℃; for 2h;	95.25%

O-ethylhydroxylamine hydrochloride (3332-29-4) + CYTIDINE (65-46-3) → N4-ethoxycytidine (1228271-25-7)

Conditions	Yield
With pyridine at 100℃;	97%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + CYTIDINE (65-46-3) → 3',5'-O-[(1,1,3,3-tetraisopropyl)-1,3-disiloxanediyl]cytidine (69304-42-3)

Conditions	Yield
With pyridine	96%
With pyridine	92%
With pyridine for 4h; cooling;	92%

acetic anhydride (108-24-7) + CYTIDINE (65-46-3) → N-acetylcytidine (3768-18-1)

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%

benzoyl chloride (98-88-4) + CYTIDINE (65-46-3) → N4-benzoylcytidine (13089-48-0)

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%

4-chlorobenzoyl chloride (586-75-4) + CYTIDINE (65-46-3) → N4-p-bromobenzoylcytidine (1386977-58-7)

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%

acetone (67-64-1) + CYTIDINE (65-46-3) → 2',3'-O-isopropylidenecytidine (362-42-5)

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%

toluene-4-sulfonic acid (104-15-4) + CYTIDINE (65-46-3) → 2',3'-O-isopropylidenecytidine (362-42-5)

Conditions	Yield
In acetone for 6h; Inert atmosphere;	95%

Upstream product

• 27391-03-3 N⁴-acetyl-O^2'_,O3'_,O5'-tribenzoyl-cytidine 
• 5746-18-9 1-methyl-4-carboxypyridinium chloride 
• 22886-36-8 C₂'p5'A 
• 4833-63-0 adenylyl 3'-5' cytidine 
• 14735-76-3 UpC 
• 23624-64-8 N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 951-77-9 2'-Deoxycytidine 
• 3181-38-2 2’,3’,5’-tri-O-acetylinosine 
• 31652-74-1 cytidine 2',3',5'-tri-O-benzoate 
• 800379-05-9 1-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 4-(O-benzyloxime) 
• 473910-24-6 [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 

Downstream Products

• 20594-00-7 3'-O-Methylcytidine 
• 2140-72-9 2'-O-methylcytidine 
• 10578-79-7 4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one 
• 2140-64-9 N³-methylcytidine 
• 2140-61-6 5-methylcytidine 
• 36207-55-3 N³,4-ethenocytidine hydrochloride 
• 69304-42-3 3',5'-O-[(1,1,3,3-tetraisopropyl)-1,3-disiloxanediyl]cytidine 
• 140679-67-0 4-N,5'-O-bis(4,4'-dimethoxytrityl)cytidine 
• 112897-99-1 5'-O-(4,4'-dimethoxytrityl)-cytidine 
• 143294-15-9 4-N-<2-<(tert-butyldiphenylsiloxy)methyl>benzoyl>-cytidine 
• 3768-18-1 N-acetylcytidine 
• 80015-55-0 2'-O-(4-methoxybenzyl)cytidine 
• 2140-69-4 3-methyluridine 
• 88121-72-6 N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine 

Relevant articles and documents

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Meteorite-catalyzed intermoleculartrans-glycosylation produces nucleosides under proton beam irradiation

Di-glycosylated adenines act as glycosyl donors in the intermoleculartrans-glycosylation of pyrimidine nucleobases under proton beam irradiation conditions. Formamide and chondrite meteorite NWA 1465 increased the yield and the selectivity of the reaction

DIVERSE AND FLEXIBLE CHEMICAL MODIFICATION OF NUCLEIC ACIDS

The present invention provides a method for chemically modifying a nucleic acid molecule using sulfinate reagents to increase stability in vitro and in vivo. Screening methods for nucleobase modifications that reduce cleavage of a nucleic acid molecule by a nuclease are also provided.

Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds

Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.