3'-O-Methylcytidine

Base Information

• Chemical Name: 3'-O-Methylcytidine
• CAS No.: 20594-00-7
• Molecular Formula: C10H15N3O5
• Molecular Weight: 257.246
• DSSTox Substance ID: DTXSID90595374
• Nikkaji Number: J120.783K
• Wikidata: Q82490374
• Mol file: 20594-00-7.mol

Synonyms:3'-O-Methylcytidine;20594-00-7;Cytidine, 3'-O-methyl-;4-amino-1-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]pyrimidin-2-one;3'-(O-METHYL)CYTIDINE;4-amino-1-((2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxytetrahydrofuran-2-yl)pyrimidin-2(1H)-one;3'-O-Methyl-D-cytidine;SCHEMBL9465863;DTXSID90595374;CHEBI:194274;RZJCFLSPBDUNDH-ZOQUXTDFSA-N;4-amino-1-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-1,2-dihydropyrimidin-2-one;MFCD00057449;AKOS027337552;BP-58839;F13608;A855670;BRD-K73748970-001-01-5

Chemical Property of 3'-O-Methylcytidine

Chemical Property:

• PSA: 119.83000
• LogP: -1.32770
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 257.10117059
• Heavy Atom Count: 18
• Complexity: 397

Purity/Quality:

97% ^*data from raw suppliers

3'-O-Methylcytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(OC(C1O)N2C=CC(=NC2=O)N)CO
• Isomeric SMILES: CO[C@@H]1[C@H](O[C@H]([C@@H]1O)N2C=CC(=NC2=O)N)CO

Technology Process of 3'-O-Methylcytidine

There total 5 articles about 3'-O-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: 60.0%

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9,58970-16-4) + N3-methylcytidine (2140-64-9)

Guidance literature:

With copper acetylacetonate; In N,N-dimethyl-formamide; at 70 ℃; for 1h;

DOI:10.1021/jo01307a026

Reference yield: 43.0%

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9,58970-16-4)

Guidance literature:

With magnesium(II) acetylacetonate; In methanol; N,N-dimethyl-formamide; at 70 ℃; for 1h; Product distribution; absence of metal ion;

DOI:10.1246/bcsj.59.2947

Reference yield: 14.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9,58970-16-4)

Guidance literature:

With tin(ll) chloride; In methanol; 1,2-dimethoxyethane; for 0.333333h; Ambient temperature;

DOI:10.1002/hlca.19960790808

upstream raw materials:

diazomethane

CYTIDINE

trimethylsulphonium hydroxide

trimethylphenylammonium hydroxide

Downstream raw materials:

3'-O-methyl-5'-O-(monomethoxytrityl)-N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine

Refernces

• 1、 Quaedflieg, Peter J. L. M.,Heiden, Arthur P. van der,Koole, Leo H.,Coenen, Annie J. J. M.,Wal, Sjoerd van der,Meijer, Emmo M.. "Synthesis and Conformational Analysis of Phosphate-Methylated RNA Dinucleotides". . p. 5846 - 5859. Retrieved 2007/10/02.
• 2、 Dudycz, Lech,Kotlicki, Andrzej,Shugar, David. "MECHANISM OF METHYLATION OF NUCLEOSIDE SUGAR HYDROXYL GROUPS BY DIAZOMETHANE IN THE PRESENCE OF STANNOUS CHLORIDE". . p. 31 - 38. Retrieved 2007/10/02.