ChemicalBook > CAS DataBase List > 2'-C-Methylcytidine

2'-C-Methylcytidine

Product Name: 2'-C-Methylcytidine
CAS No.: 20724-73-6
Chemical Name: 2'-C-Methylcytidine
Synonyms: NM-107;CS-2055;-C-Methylcytidine;2''-METHYLCYTIDINE;2'-C-METHYLCYTIDINE;2’-C-Methyl cytidine;NM107, 10 mM in DMSO;2'-CMethyl-D-cytidine;2’-β-C-Methylcytidine;Cytidine, 2'-C-methyl-
CBNumber: CB5732016
Molecular Formula: C10H15N3O5
Formula Weight: 257.24
MOL File: 20724-73-6.mol

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2'-C-Methylcytidine Property

Melting point:: 243-245°C
Boiling point:: 523.9±60.0 °C(Predicted)
Density: 1.72±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: H2O: >20mg/mL
pka: 13.53±0.70(Predicted)
form: powder
color: white to off-white
Water Solubility: H2O: >20mg/mL
InChI: InChI=1S/C10H15N3O5/c1-10(17)7(15)5(4-14)18-8(10)13-3-2-6(11)12-9(13)16/h2-3,5,7-8,14-15,17H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,10-/m1/s1
InChIKey: PPUDLEUZKVJXSZ-VPCXQMTMSA-N
SMILES: OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@](C)(O)[C@@H]1O

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: M4949
Product name: 2’-C-Methylcytidine
Purity: ≥95% (HPLC), powder
Packaging: 5mg
Price: $101
Updated: 2025/07/31

Sigma-Aldrich

Product number: M4949
Product name: 2’-C-Methylcytidine
Purity: ≥95% (HPLC), powder
Packaging: 25mg
Price: $399
Updated: 2025/07/31

Cayman Chemical

Product number: 22887
Product name: 2'-C-Methylcytidine
Purity: ≥98%
Packaging: 5mg
Price: $86
Updated: 2024/03/01

Cayman Chemical

Product number: 22887
Product name: 2'-C-Methylcytidine
Purity: ≥98%
Packaging: 10mg
Price: $161
Updated: 2024/03/01

Cayman Chemical

Product number: 22887
Product name: 2'-C-Methylcytidine
Purity: ≥98%
Packaging: 25mg
Price: $336
Updated: 2024/03/01

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2'-C-Methylcytidine Chemical Properties,Usage,Production

Description

2''-C-Methylcytidine (2CMC) is a ribonucleoside with broad-spectrum antiviral activity. It reduces the number of viral plaques in BHK-21 cells infected with dengue type 2, reovirus type 1, West Nile, and yellow fever RNA viruses with EC₅₀ values of 95, 26, 80, and 75 μM, respectively. 2CMC inhibits hepatitis C virus (HCV) replication (EC₅₀ = 2.2 μM in a replicon assay) and protects MDBK cells from infection with bovine virus diarrhea virus (BVDV; EC₅₀ = 2.2 μM) and human coronavirus (HCoV; EC₅₀ = 90 μM). It also reduces infectious virus yield in BHK-21 cells infected with foot-and-mouth disease virus (FMDV; EC₅₀ = 6.4 μM) and swine vesicular disease virus (SVDV; EC₅₀ = 45.2 μM). In vivo, 2CMC reduces viral shedding to undetectable levels in a mouse model of persistent norovirus infection.

Chemical Properties

White to Off-White Powder

Uses

2’-C-Methyl Cytidine (cas# 20724-73-6) is a compound useful in organic synthesis.

Biochem/physiol Actions

2′-C-Methylcytidine is a potent inhibitor of the HCV NS5B RNA polymerase. 2′-C-Methylcytidine was the first nucleoside NS5B inhibitor that showed clinical efficacy. 2′-C-Methylcytidine was found to be effective against the 17D vaccine strain of yellow fever virus YFV in cell culture.

Synthesis

220503-64-0

20724-73-6

Example 2: Synthesis of 2'-C-methylcytidine (4) A methanolic solution of saturated NH3 (250 mL) was added to the compound of Example 1 (5.4 g, 8.0 mmol) and the reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was removed by rotary evaporation and the residue was purified by silica gel column chromatography with the eluent CH2Cl2/MeOH/NH3 (8.3:1.5:0.2) to afford 4-amino-1-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one as a white solid, yield 80%. TLC analysis (CH2Cl2/MeOH/NH3, 8.3:1.5:0.2): Rf = 0.13. 1H NMR (500 MHz, MeOD) δ: 8.13 (d, 1H, J6,5 = 7.5 Hz, H-6), 6.02 (s, 1H, H-1'), 5.89 (d, 1H, J5,6 = 7.5 Hz, H-5), 3.99-3.96 (dd, J = 1.9 Hz, 12.45 Hz, 1H, H-5'), 3.93 -3.91 (m, 1H, H-4'), 3.82-3.77 (m, 2H, H-3' and H-5''), 1.10 (s, 3H, -CH3). 13C NMR (125 MHz, MeOD) δ: 167.5 (C-4), 158.5 (C-2), 143.1 (C-6), 95.9 (C-5), 93.9 (C-1'), 83.8 (C-4'), 80.2 (C-2'), 73.7 (C-3'), 60.8 (C-5'), 20.5 (-CH3). HRMS (ESI+) calculated value C10H15N3O5Na [M + Na]+ 280.0904, measured value 280.0901.

References

[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 18, p. 5158 - 5174
[2] Patent: WO2015/158913, 2015, A1. Location in patent: Page/Page column 37

2'-C-Methylcytidine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2'-C-Methylcytidine manufacturers

NewCan Biotech Limited

Product: 2'-C-methylCytidine 20724-73-6
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 100g
Release date: 2024-06-03

Career Henan Chemical Co

Product: 2'-C-Methylcytidine 20724-73-6
Price: US $5.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 1ton
Release date: 2019-08-05

20724-73-6, 2'-C-MethylcytidineRelated Search:

Cytidine 5’-monophosphate 5-METHYLCYTOSINE Cytidine Cytosine 5-Fluorocytidine Fluorocytosine Cytidine-5'-triphosphate disodium salt dihydrate 5-Azacytidine Cytarabine 2'-C-Methylguanosine 2'-C-Methyladenosine 2'-METHYLCYTIDINE-5'-TRIPHOSPHATE, DIAMMONIUM SALT Valopicitabine 2'-METHYLCYTIDINE-5'-MONOPHOSPHATE, DIAMMONIUM SALT 2',3',5'-Tri-O-benzoyl-2'-C-methyl-D-cytidine 2'-C-Methylcytidine

2'-C-METHYLCYTIDINE

2'-CMethyl-D-cytidine

2''-METHYLCYTIDINE

1-(2-C-Methyl-β-D-ribofuranosyl)cytosine

NM-107

2'-C-Methyl-1-β-D-ribofuranosylcytosine

-C-Methylcytidine

2'-C-METHYLCYTIDINE;NM-107;VALOPICITABINE

CS-2055

4-AMINO-1-[3,4-DIHYDROXY-5-(HYDROXYMETHYL)-3-METHYLOXOLAN-2-YL]PYRIMIDIN-2-ONE

Cytidine, 2'-C-methyl-

2’-C-Methyl cytidine, 2’-C-Methyl-1-β-D-ribofuranosyl cytosine

2’-β-C-Methylcytidine

2'-C-Methylcytidine USP/EP/BP

4-Amino-1-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one

2’-b-C-Methyl cytidine NM107, HCV drug

2’-b-C-Methyl cytidine

4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one

NM 107,inhibit,Inhibitor,HCV,Hepatitis C virus,NM107

2’-C-Methyl cytidine

NM107, 10 mM in DMSO

NM107 (2'-C-Methylcytidine

20724-73-6

C10H15N3O5

Bases & Related Reagents

Nucleotides