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2'-O-(2-Methoxyethyl)-5-methyluridine

2'-O-(2-Methoxyethyl)-5-methyluridine Structure
CAS No.
163759-49-7
Chemical Name:
2'-O-(2-Methoxyethyl)-5-methyluridine
Synonyms
MOE-mrU;2'-O-MOE-Tr;2'-O-MOE-Tr;2'-MOE-5-Me-rU;5-Me-2'-O-MOE U;5-Me-2'-O-MOE U;5-Me-2'-O-MOE-Ur;2'-O-MOE-5-Me-rU;5-Me-2'-O-MOE-Me-U;2'-MOE-5-Me-Uridine
CBNumber:
CB82510024
Molecular Formula:
C13H20N2O7
Molecular Weight:
316.31
MOL File:
163759-49-7.mol
MSDS File:
SDS
Modify Date:
2023/11/28 11:20:42

2'-O-(2-Methoxyethyl)-5-methyluridine Properties

Melting point 115.5-116.5 °C
Density 1.41
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
form Solid
pka 9.55±0.10(Predicted)
color Off-White
Stability Hygroscopic
InChI InChI=1S/C13H20N2O7/c1-7-5-15(13(19)14-11(7)18)12-10(21-4-3-20-2)9(17)8(6-16)22-12/h5,8-10,12,16-17H,3-4,6H2,1-2H3,(H,14,18,19)/t8-,9-,10-,12-/m1/s1
InChIKey NEVQCHBUJFYGQO-DNRKLUKYSA-N
SMILES OC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)[C@H](OCCOC)[C@@H]1O

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H320-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338

2'-O-(2-Methoxyethyl)-5-methyluridine Chemical Properties,Uses,Production

Uses

2'-O-(2-Methoxyethyl)-5-methyluridine is a protected uridine derivative (U829910) and nucleoside used in the preparation of synthetic nucleic acids.

Application

2'-O-(2-Methoxyethyl)-5-methyluridine (2'-MOE-5-Methyluridine) is a uridine nucleoside that is a combination of amidite with 5-methyluridine. 2'-MOE-5-Methyluridine is an intermediate in the synthesis of oligonucleotides, which are synthesized from phosphoramidites. Its analog 5'-O-DMT-2'-O-(2-methoxyethyl)-5-methyluridine is a potent compound used in research of RNA viruses, particularly hepatitis C virus and picornaviruses.

Synthesis

1.jpg
2,2'-Anhydro-5-methyluridine (195 g, 0.81 M), tris(2-methoxyethyl)borate (231 g, 0.98 M) and 2-methoxyethanol (1.2 L) were added to a 2 L stainless steel pressure vessel and placed in a pre-heated oil bath at 160°C. After heating for 48 hours at 155-160°C, the vessel was opened and the solution evaporated to dryness and triturated with methanol (200 mL). The residue was suspended in hot acetone (1 L). The insoluble salts were filtered, washed with acetone (150 mL) and the filtrate evaporated. The residue (280 g) was dissolved in CH3CN (600 mL) and evaporated. A silica gel column (3 kg) was packed in CH2Cl2/ acetone/methanol (20:5:3) containing 0.5% Et3NH. The residue was dissolved in CH2Cl2 (250 mL) and adsorbed onto silica (150 g) prior to loading onto the column. The product was eluted with the packing solvent to give product. Yield 160 g, 63%.

2'-O-(2-Methoxyethyl)-5-methyluridine Preparation Products And Raw materials

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2'-O-(2-Methoxyethyl)-5-methyluridine 5-Me-2'-O-MOE U Uridine, 2'-O-(2-Methoxyethyl)-5-Methyl- 5-Me-2'-O-MOE Uridine 2'-O-(2-Methoxyethy)-5-methyluridine 2'-O-(2-Methoxyethyl)-5-Methyl-uridine, >97% 1-[4-HYDROXY-5-(HYDROXYMETHYL)-3-(2-METHOXYETHOXY)OXOLAN-2-YL]-5-METHYL-3H-PYRIMIDINE-2,4-DIONE 2'-O-MOE-5-Methyluridin 2'-O-MOE-Tr 2'-O-Methoxyethyl-thyminde 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 2'-MOE-5-Me-Uridine 2’-MOE-5-Methyluridine 5-Me-2'-O-MOE-Ur MOE-mrU 2'-MOE-5-Me-rU 2'-O-Methoxyethyl-5-methyluridine 2'-O-MOE-5-Me-rU 2'-O-(2-Methoxyethyl)-5-methyluridine 2’-O-(2-Methoxyethy)-5-methyl uridine 5-Me-2'-O-MOE U 2'-MOE-5-Methyluridine 2'-O-Methoxyethyl-thymine 5-Me-2'-O-MOE-Me-U 2'-O-MOE-Tr 2'-o-Methoxyethyl-5-methyluridine 163759-49-7 Modified(deoxy)nucleoside Nucleosides-2'-O-MOE Nucleosides