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

2'-O-(2-Methoxyethyl)-5-methyluridine Basic information
Product Name:2'-O-(2-Methoxyethyl)-5-methyluridine
Synonyms: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
CAS:163759-49-7
MF:C13H20N2O7
MW:316.31
EINECS:500-100-4
Product Categories:
Mol File:163759-49-7.mol
2'-O-(2-Methoxyethyl)-5-methyluridine Structure
2'-O-(2-Methoxyethyl)-5-methyluridine Chemical 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
pka9.55±0.10(Predicted)
color Off-White
Stability:Hygroscopic
InChIInChI=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
InChIKeyNEVQCHBUJFYGQO-DNRKLUKYSA-N
SMILESOC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)[C@H](OCCOC)[C@@H]1O
Safety Information
MSDS Information
2'-O-(2-Methoxyethyl)-5-methyluridine Usage And Synthesis
Uses2'-O-(2-Methoxyethyl)-5-methyluridine is a protected uridine derivative (U829910) and nucleoside used in the preparation of synthetic nucleic acids.
Synthesis1.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
Raw materialstris(2-methoxyethyl) orthoborate-->2,2'-Anhydro-5-methyluridine-->2-Methoxyethanol
2'-O-(2-Methoxyethyl)guanosine 5'-O-(4,4-Dimethoxytrityl)-2'-O-methyl-N-isobutyrylguanosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 2'-O-MOE-ADENOSINE (2R,3R,4R,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)-4-(2-METHOXYETHOXY)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE 2'-O-(2-Methoxyethyl)uridine 2'-O-Methylguanosine 2'-O-(2-Methoxyethyl)cytidine 2'-O-Methyladenosine DMT-2'-F-DC(AC) AMIDITE 0.25G, AB, SINGL N4-Benzoyl-5'-O-DMT-2'-O-methyl-5-methylcytidine 3'-CE phosphoramidite N-blocked-5'-O-DMT-2'-O-Me CED cytosine phosphoramidite 2'-O-MOE-A(Bz)-3'-phosphoramidite 5'-O-(4,4-Dimethoxytrityl)-2'-deoxy-2'-fluorouridine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 2’-O-Methyl-rA(N-Bz)phosphoramidite DMT-2μ-O-Me-rG(ib) amidite 2'-O-Methylcytidine
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