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2'-O-(2-Methoxyethyl)cytidine

2'-O-(2-Methoxyethyl)cytidine Structure
CAS No.
223777-16-0
Chemical Name:
2'-O-(2-Methoxyethyl)cytidine
Synonyms
2'-MOE-C;2'-MOE-rC;2'-O-MOE-rC;2'-O-MOE-Cr;2'-MOE-Cytidine;2'-O-MOE Cytidine;2'-O-MOE Cytidine;2'-O-(2-mthoxyethyl)Cytidine;2'-O-(2-Methoxyethyl)cytidine;2'-O-(2-Methoxyethyl)cytidine
CBNumber:
CB32510559
Molecular Formula:
C12H19N3O6
Molecular Weight:
301.3
MOL File:
223777-16-0.mol
Modify Date:
2024/7/2 8:55:06

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

Boiling point 535.3±60.0 °C(Predicted)
Density 1.57±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO : 250 mg/mL (829.74 mM)
pka 13.36±0.70(Predicted)
form Solid
color White to off-white
InChI InChI=1S/C12H19N3O6/c1-19-4-5-20-10-9(17)7(6-16)21-11(10)15-3-2-8(13)14-12(15)18/h2-3,7,9-11,16-17H,4-6H2,1H3,(H2,13,14,18)/t7-,9-,10-,11-/m1/s1
InChIKey YKOGMMXZKKVMBT-QCNRFFRDSA-N
SMILES OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](OCCOC)[C@@H]1O

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338

2'-O-(2-Methoxyethyl)cytidine Chemical Properties,Uses,Production

Uses

A cytidine derivative as building blocks for cross-linking oligonucleotides.

Synthesis

2'-O-(2-Methoxyethyl)uridine could be converted into the corresponding cytidine derivative (2'-O-(2-Methoxyethyl)cytidine) by the 4-nitrophenylation[1]. 2'-O-(2-Methoxyethyl)uridine, l-methylpyrrolidine, chlorotrimethylsilane and dry acetonitrile were stirred together at rt. After 1 h, the reaction mixture was cooled to 0 ℃, and trifluoroacetic anhydride was added dropwise over 5 min. After a further period of 30 rain at 0 ℃, 4-nitrophenol was added to the stirred reactants which were maintained at 0 °C. After 3 h, the products were poured into saturated aqueous sodium hydrogen carbonate, and the resulting mixture was extracted with dichloromethane. The combined organic layers were dried, and evaporated under reduced pressure. Concentrated aqueous ammonia was added to a stirred solution of the residue in dioxane, contained in a sealed flask that was then heated at 55°C for 24 h. The resulting yellow solution was concentrated under reduced pressure and the residue was evaporated with absolute ethanol. The products were fractionated by short column chromatography on silica gel and were evaporated under reduced pressure to give 2'-O-(2-Methoxyethyl)cytidine as an off-white solid.
2'-O-(2-Methoxyethyl)cytidine

References

[1] Urtzi et al. "Conversion of uridine into 2′-O-(2-methoxyethyl)uridine and 2′-O-(2-methoxyethyl)cytidine." Tetrahedron (1999).

2'-O-(2-Methoxyethyl)cytidine Preparation Products And Raw materials

Raw materials

Preparation Products

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2'-O-(2-Methoxyethyl)cytidine 2'-O-MOE Cytidine 4-AMINO-1-[(2R,3R,4R,5R)-4-HYDROXY-5-(HYDROXYMETHYL)-3-(2-METHOXYETHOXY)OXOLAN-2-YL]PYRIMIDIN-2-ONE 2'-O-(2-Methoxyethyl)-cytidine, >97% 4-AMINO-1-[4-HYDROXY-5-(HYDROXYMETHYL)-3-(2-METHOXYETHOXY)OXOLAN-2-YL]PYRIMIDIN-2-ONE 4-amino-1-[(2R,3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl]pyrimidin-2-one Cytidine, 2'-O-(2-methoxyethyl)- 2'-O-MOE-rC 2'-MOE-Cytidine 2'-O-MOE-Cr 2'-MOE-rC 2'-MOE-C 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl]pyrimidin-2-one 2'-O-(2-mthoxyethyl)Cytidine 2'-O-(2-Methoxyethyl)cytidine 2'-O-MOE Cytidine 223777-16-0 Bases & Related Reagents Carbohydrates & Derivatives Heterocycles Nucleotides