2'-C-Methylcytidine

Base Information

• Chemical Name: 2'-C-Methylcytidine
• CAS No.: 20724-73-6
• Molecular Formula: C10H15N3O5
• Molecular Weight: 257.24
• Hs Code.: 2934999090
• Mol file: 20724-73-6.mol

Synonyms:NM 107;

Chemical Property of 2'-C-Methylcytidine

Chemical Property:

• Appearance/Colour: White to Off-White Powder
• Melting Point: 243-245 °C
• Boiling Point: 523.9 °C at 760 mmHg
• PKA: 13.53±0.70(Predicted)
• Flash Point: 270.7 °C
• PSA: 130.83000
• Density: 1.72 g/cm³
• LogP: -1.59170
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: H2O: >20mg/mL

Purity/Quality:

98%,99%, ^*data from raw suppliers

2’-C-MethylCytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2'-C-Methylcytidine

There total 1 articles about 2'-C-Methylcytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9) → 2'-C-methylcytidine (20724-73-6,115494-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / CH₃ONa; methanol / 20 °C

With methanol; sodium methylate;

DOI:10.1081/NCN-200060112

Reference yield: 90.0%

benzyl chloroformate (501-53-1,94274-21-2) + 2'-C-methylcytidine (20724-73-6,115494-60-5) → 2′-C-methyl-N4-benzyloxycarbonylcytidine

Guidance literature:

2'-C-methylcytidine; With pyridine; chloro-trimethyl-silane; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

benzyl chloroformate; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c5ob00427f

Reference yield: 89.0%

mono-4-methoxytrityl chloride (14470-28-1) + 2'-C-methylcytidine (20724-73-6,115494-60-5) → 1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl]-4-[[(4-methoxyphenyl)-diphenyl-methyl]amino]pyrimidin-2-one

Guidance literature:

2'-C-methylcytidine; With pyridine; chloro-trimethyl-silane; at 0 - 20 ℃; for 4h;

mono-4-methoxytrityl chloride; With dmap; at 50 ℃; for 48h;

upstream raw materials:

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine

Downstream raw materials:

5-O-(4-chlorophenyl methoxydimethylglycinylphosphate)-(2-C-methyl-β-D-ribofuranosyl)cytosine

C₃₁H₃₃N₃O₇

ethyl (2S)-2-{[{[(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl]methoxy}(4-chlorophenoxy)phosphoryl]amino}propanoate

5'-O-[[[(1S)-1-methyl-2-(1-methylethoxy)-2-oxoethyl]amino]phenoxyphosphinyl]-2'-C-methylcytidine

Refernces