5'-O-(4,4'-Dimethoxytrityl)uridine

Base Information

• Chemical Name: 5'-O-(4,4'-Dimethoxytrityl)uridine
• CAS No.: 81246-79-9
• Molecular Formula: C30H30 N2 O8
• Molecular Weight: 546.577
• ChEMBL ID: CHEMBL3798292
• DSSTox Substance ID: DTXSID301250023
• Nikkaji Number: J806.018E
• Mol file: 81246-79-9.mol

Synonyms:Uridine,5'-O-[a,a-bis(p-methoxyphenyl)benzyl]- (7CI);5'-O-(4,4'-Dimethoxytrityl)uridine

Chemical Property of 5'-O-(4,4'-Dimethoxytrityl)uridine

Chemical Property:

• Melting Point: 111-112 °C(Solv: ethyl acetate (141-78-6))
• PKA: 9.39±0.10(Predicted)
• PSA: 132.24000
• Density: 1.343±0.06 g/cm3(Predicted)
• LogP: 2.18170
• Storage Temp.: Store at 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 546.20021592
• Heavy Atom Count: 40
• Complexity: 868

Purity/Quality:

97% ^*data from raw suppliers

5''-O-(4,4''-Dimethyltrityl)uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OCC4C(C(C(O4)N5C=CC(=O)NC5=O)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=CC(=O)NC5=O)O)O

Technology Process of 5'-O-(4,4'-Dimethoxytrityl)uridine

There total 12 articles about 5'-O-(4,4'-Dimethoxytrityl)uridine 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: 98.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + uridine (58-96-8) → 5'-dimethoxytrityluridine (81246-79-9)

Guidance literature:

With pyridine; at 20 ℃; for 1h;

DOI:10.1021/ja909708a

Reference yield: 87.0%

uridine (58-96-8) + 4,4'-((benzyloxy)(phenyl)methylene)bis(methoxybenzene) → 5'-dimethoxytrityluridine (81246-79-9)

Guidance literature:

With cerium(IV) trifluoromethanesulfonate; diethylazodicarboxylate; In acetonitrile; at 20 ℃; for 2h; Molecular sieve;

DOI:10.1139/V10-042

Reference yield: 81.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + uridine → 5'-dimethoxytrityluridine (81246-79-9)

Guidance literature:

With pyridine; triethylamine; at 20 ℃;

DOI:10.1039/c7ob02296d

upstream raw materials:

4,4'-dimethoxytrityl chloride

uridine

5'-O-(4,4'-dimethoxytrityl)-2'-O-[2-(N,N-dimethylcarbamoyl)ethyl]uridine

2'-O-methylthiomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}uridine

5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}uridine

5'-O-(4,4'-dimethoxytrityl)-2'-O-(levulinyl)uridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

5'-O-(4,4'-dimethoxytrityl)-3'-O-(levulinyl)uridine

Refernces

• 1、 Berney, Mark,Fay, Ellen M.,Manoj, Manav T,McGouran, Joanna F.. "5’-Phosphorylation Increases the Efficacy of Nucleoside Inhibitors of the DNA Repair Enzyme SNM1A". supporting information. . Retrieved 2022/01/13.
• 2、 Meyer, Andreas,Dechert, Sebastian,Dey, Surjendu,H?bartner, Claudia,Bennati, Marina. "Measurement of Angstrom to Nanometer Molecular Distances with 19F Nuclear Spins by EPR/ENDOR Spectroscopy". supporting information. p. 373 - 379. Retrieved 2019/11/22.