2'-O-[(4-Methoxyphenyl)methyl]uridine

Base Information

• Chemical Name: 2'-O-[(4-Methoxyphenyl)methyl]uridine
• CAS No.: 80015-57-2
• Molecular Formula: C17H20N2O7
• Molecular Weight: 364.355
• DSSTox Substance ID: DTXSID00559280
• Nikkaji Number: J2.479.307I
• Wikidata: Q82441946
• Mol file: 80015-57-2.mol

Synonyms:80015-57-2;2'-O-[(4-Methoxyphenyl)methyl]uridine;DTXSID00559280

Chemical Property of 2'-O-[(4-Methoxyphenyl)methyl]uridine

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 364.12705098
• Heavy Atom Count: 26
• Complexity: 547

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)COC2C(C(OC2N3C=CC(=O)NC3=O)CO)O
• Isomeric SMILES: COC1=CC=C(C=C1)CO[C@@H]2[C@@H]([C@H](O[C@H]2N3C=CC(=O)NC3=O)CO)O

Technology Process of 2'-O-[(4-Methoxyphenyl)methyl]uridine

There total 4 articles about 2'-O-[(4-Methoxyphenyl)methyl]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: 21.0%

p-Methoxybenzyl bromide (2746-25-0) + 2,3’-O-dibutylstannyleneuridine (42822-78-6) → 3'-O-(4-methoxybenzyl)uridine (85193-75-5) + 2'-O-(4-methoxybenzyl)uridine (80015-57-2)

Guidance literature:

In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1021/jo00175a010

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → 2'-O-(4-methoxybenzyl)uridine (80015-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrazine / diethyl ether / 0 - 10 °C

2: HgO, KOH / methanol / 1 h

3: 23 percent / SnCl₂*H₂O / dimethylformamide; CH₂Cl₂ / 2 h / 45 °C

With potassium hydroxide; tin(ll) chloride; mercury(II) oxide; hydrazine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82051-2

Reference yield:

(4-methoxybenzylidene)-hydrazine (5953-85-5,214466-47-4) → 2'-O-(4-methoxybenzyl)uridine (80015-57-2)

Guidance literature:

Multi-step reaction with 2 steps

1: HgO, KOH / methanol / 1 h

2: 23 percent / SnCl₂*H₂O / dimethylformamide; CH₂Cl₂ / 2 h / 45 °C

With potassium hydroxide; tin(ll) chloride; mercury(II) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82051-2

upstream raw materials:

p-Methoxybenzyl bromide

2,3’-O-dibutylstannyleneuridine

4-methoxy-benzaldehyde

(4-methoxybenzylidene)-hydrazine

Downstream raw materials:

uridine

C₄₇H₄₂ClN₃O₁₂P^(1-)*C₈H₂₀N⁽¹⁺⁾

Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester