N³-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine

Base Information

• Chemical Name: N³-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine
• CAS No.: 304442-32-8
• Molecular Formula: C₂₁H₂₆N₂O₉
• Molecular Weight: 450.445
• Mol file: 304442-32-8.mol

Synonyms:N³-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine

Chemical Property of N³-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N³-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine

There total 1 articles about N³-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine 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: 74.0%

bromoacetic acid methyl ester (96-32-2) + N3-benzyloxymethyl-5-methyluridine (165381-68-0) → N3-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine (304442-32-8) + [(2R,3S,4R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-acetic acid methyl ester

Guidance literature:

N³-benzyloxymethyl-5-methyluridine; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

bromoacetic acid methyl ester; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/ol027131k

Reference yield:

N3-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine (304442-32-8) → Succinic acid mono-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-dimethylcarbamoylmethoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / Pd on carbon / methanol / 16 h / 1551.49 Torr

1.2: 95 percent / Et₃N / methanol / 2 h / Heating

2.1: 59 percent / dimethylaminopyridine / pyridine / 12 h

3.1: 95 percent / tetrahydrofuran / 18 h / 20 °C

4.1: 96 percent / DMAP; triethyl amine / 1,2-dichloro-ethane / 20 °C

With dmap; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane;

DOI:10.1021/ol027131k

Reference yield:

N3-benzyloxymethyl-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine (304442-32-8) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine (304442-33-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen / Pd on carbon / methanol / 16 h / 1551.49 Torr

1.2: 95 percent / Et₃N / methanol / 2 h / Heating

2.1: 59 percent / dimethylaminopyridine / pyridine / 12 h

With dmap; hydrogen; palladium on activated charcoal; In pyridine; methanol;

DOI:10.1021/ol027131k

upstream raw materials:

bromoacetic acid methyl ester

N³-benzyloxymethyl-5-methyluridine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxy-2-oxoethyl)-5-methyluridine

5'-O-(4,4'-dimethoxytrityl)-2'-O-[2-(dimethylamino)-2-oxoethyl]-5-methyluridine