2'-O-(2-Methoxyethyl)-cytidine

Base Information

• Chemical Name: 2'-O-(2-Methoxyethyl)-cytidine
• CAS No.: 223777-16-0
• Molecular Formula: C12H19N3O6
• Molecular Weight: 301.29576
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30454431
• Nikkaji Number: J1.103.879D
• Wikidata: Q72489814
• Mol file: 223777-16-0.mol

Synonyms:2'-O-(2-Methoxyethyl)-cytidine;223777-16-0;2'-O-(2-METHOXYETHYL)CYTIDINE;Cytidine, 2'-O-(2-methoxyethyl)-;4-AMINO-1-[(2R,3R,4R,5R)-4-HYDROXY-5-(HYDROXYMETHYL)-3-(2-METHOXYETHOXY)OXOLAN-2-YL]PYRIMIDIN-2-ONE;4-amino-1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;SCHEMBL1054903;DTXSID30454431;YKOGMMXZKKVMBT-QCNRFFRDSA-N;2/'-O-(2-Methoxyethyl)-cytidine;MFCD17215637;AKOS015900783;AM10133;HY-W048496;AC-24670;BP-58652;BS-49646;PD158394;CS-0100789;F12192;J-700322

Chemical Property of 2'-O-(2-Methoxyethyl)-cytidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.631
• Boiling Point: 535.262 °C at 760 mmHg
• PKA: 13.36±0.70(Predicted)
• Flash Point: 277.517 °C
• PSA: 130.05000
• Density: 1.573 g/cm³
• LogP: -1.54990
• Storage Temp.: 2-8°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 301.12738533
• Heavy Atom Count: 21
• Complexity: 441

Purity/Quality:

98%, ^*data from raw suppliers

2''-O-(2-Methoxyethyl)cytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCOC1C(C(OC1N2C=CC(=NC2=O)N)CO)O
• Isomeric SMILES: COCCO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O
• Description: 2'-O-(2-Methoxyethyl)-cytidine is a cytidine derivative that can be used as a building block for crosslinking oligonucleotides. 2'-O-(2-Methoxyethyl)-cytidine is also used as a texturizing agent in food products.
• Uses: A cytidine derivative as building blocks for cross-linking oligonucleotides.

Technology Process of 2'-O-(2-Methoxyethyl)-cytidine

There total 7 articles about 2'-O-(2-Methoxyethyl)-cytidine 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: 84.0%

2'-O-(2-methoxyethyl)uridine (223777-15-9) → 2'-O-(2-methoxyethyl)cytidine (223777-16-0)

Guidance literature:

2'-O-(2-methoxyethyl)uridine; With 1-Methylpyrrolidine; chloro-trimethyl-silane; In acetonitrile; at 20 ℃; for 1h;

With trifluoroacetic anhydride; In acetonitrile; at 0 ℃; for 0.0833333h;

With 4-nitro-phenol; sodium bicarbonate; ammonia; water; more than 3 stages;

Reference yield: 84.0%

1-Methylpyrrolidine (120-94-5) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2'-O-(2-methoxyethyl)uridine (223777-15-9) → 2'-O-(2-methoxyethyl)cytidine (223777-16-0)

Guidance literature:

With chloro-trimethyl-silane; ammonia; trifluoroacetic anhydride; In 1,4-dioxane; ethanol; acetonitrile;

Reference yield:

1-[(2R,3R,4R,5R)-3-(2-Methoxy-ethoxy)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl]-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one → 2'-O-(2-methoxyethyl)cytidine (223777-16-0)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 55 ℃; for 24h;

DOI:10.1016/S0040-4020(99)00229-X

upstream raw materials:

1-Methylpyrrolidine

4-nitro-phenol

2'-O-(2-methoxyethyl)uridine

2,2'-Anhydrouridine

Downstream raw materials:

N-{1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-6-formyl-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N-{1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N⁴-benzoyl-2'-O-(2-methoxyethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-dimethoxytrityl-6-formylcytidine

N⁴-benzoyl-2'-O-(2-methoxyethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-dimethoxytritylcytidine

Refernces

• 1、 -. "2′-Substituted RNA preparation". . . Retrieved 2008/06/13.
• 2、 Legorburu, Urtzi,Reese, Colin B.,Song, Quanlai. "Conversion of uridine into 2'-O-(2-methoxyethyl)uridine and 2'-O-(2- methoxyethyl)cytidine". . p. 5635 - 5640. Retrieved 2007/10/03.