2'-O-Methylcytidine

Base Information

• Chemical Name: 2'-O-Methylcytidine
• CAS No.: 2140-72-9
• Deprecated CAS: 58970-16-4
• Molecular Formula: C10H15N3O5
• Molecular Weight: 257.246
• Hs Code.: 29349990
• UNII: 5XD9IH2G27
• DSSTox Substance ID: DTXSID50943958
• Nikkaji Number: J120.782B
• Wikidata: Q15632793
• Metabolomics Workbench ID: 53678
• ChEMBL ID: CHEMBL176605
• Mol file: 2140-72-9.mol

Synonyms:2'-O-methylcytidine;O(2')-methylcytidine

Chemical Property of 2'-O-Methylcytidine

Chemical Property:

• Melting Point: 252-253 °C
• Boiling Point: 506 °C at 760 mmHg
• PKA: 13.37±0.70(Predicted)
• Flash Point: 259.8 °C
• PSA: 119.83000
• Density: 1.68 g/cm³
• LogP: -1.32770
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO.
• XLogP3: -1.6
• 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:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(OC1N2C=CC(=NC2=O)N)CO)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O
• Uses: 2'-O-Methylcytidine is used in the preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase. Cytidine analog.

Technology Process of 2'-O-Methylcytidine

There total 23 articles about 2'-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: 99.0%

3',5'-di-O-acetyl-2'-O-methylcytidine (1085342-86-4) → 2'-O-methylcytidine (2140-72-9,58970-16-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

DOI:10.1016/j.bmc.2008.09.016

Reference yield: 96.0%

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2) → 2'-O-methylcytidine (2140-72-9,58970-16-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

Reference yield: 80.0%

N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine (73793-16-5) → 2'-O-methylcytidine (2140-72-9,58970-16-4)

Guidance literature:

With ammonia; In methanol; at 4 ℃; for 48h;

DOI:10.1021/jo00341a005

upstream raw materials:

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine

N⁴-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine

diazomethane

CYTIDINE

Downstream raw materials:

2'-O-methyl-N⁴-benzoylcytidine

N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methylcytidine

N⁴-(4,4'-dimethoxytrityl)-2'-O-methylcytidine

N⁴-acetyl-2'-O-methyl cytidine

Refernces

• 1、 Hruska et al.. "-". . p. 1099,1101,1102. Retrieved 1973.
• 2、 Kusmierek,Giziewicz,Shugar. "Preparation of O'-alkyl derivatives of cytosine and uracil nucleosides.". . p. 194 - 200. Retrieved 1973.
• 3、 Schneider, Christina,Becker, Sidney,Okamura, Hidenori,Crisp, Antony,Amatov, Tynchtyk,Stadlmeier, Michael,Carell, Thomas. "Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations". supporting information. p. 5943 - 5946. Retrieved 2018/04/30.
• 4、 -. "Sugar modified oligonucleotides". . . Retrieved 2008/06/13.