5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine

Base Information

• Chemical Name: 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine
• CAS No.: 161824-93-7
• Molecular Formula: C₂₆H₂₈N₂O₆
• Molecular Weight: 464.518

Synonyms:5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine

Chemical Property of 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine

There total 6 articles about 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-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: 82.0%

1-<2',3'-Dihydroxy-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N3-(4-methoxybenzyl)-5-methyluracil (161824-89-1) → 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N3-(4-methoxybenzyl)-5-methyluridine (161824-93-7)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; acetonitrile; at 65 ℃; for 0.5h;

DOI:10.1021/jo00103a017

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N3-(4-methoxybenzyl)-5-methyluridine (161824-93-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / tert-butyldimethylsilyl triflate

2: 98 percent / NaOMe / methanol

3: 95 percent / p-toluenesulfonic acid monohydrate / 1,2-dichloro-ethane / 1.33 h / 65 °C

4: 75 percent / NaH / 1,2-dimethoxy-ethane / 1.) r.t., 20 min, 2.) 65 deg C, 18 h

5: 96 percent / 66percent aq. dichloroacetic acid / 3 h / 9 °C

6: 82 percent / PPh₃, I₂, imidazole / toluene; acetonitrile / 0.5 h / 65 °C

With 1H-imidazole; dichloro-acetic acid; t-butyldimethylsiyl triflate; iodine; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; In methanol; 1,2-dimethoxyethane; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1021/jo00103a017

Reference yield:

2',3',5'-tri-O-benzoyluridine (3180-76-5) → 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N3-(4-methoxybenzyl)-5-methyluridine (161824-93-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / NaOMe / methanol

2: 95 percent / p-toluenesulfonic acid monohydrate / 1,2-dichloro-ethane / 1.33 h / 65 °C

3: 75 percent / NaH / 1,2-dimethoxy-ethane / 1.) r.t., 20 min, 2.) 65 deg C, 18 h

4: 96 percent / 66percent aq. dichloroacetic acid / 3 h / 9 °C

5: 82 percent / PPh₃, I₂, imidazole / toluene; acetonitrile / 0.5 h / 65 °C

With 1H-imidazole; dichloro-acetic acid; iodine; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; In methanol; 1,2-dimethoxyethane; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1021/jo00103a017

upstream raw materials:

1-<2',3'-Dihydroxy-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N³-(4-methoxybenzyl)-5-methyluracil

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2',3',5'-tri-O-benzoyluridine

1-(2'-O,3'-O-Cyclopentyl-5'-hydroxy-β-D-erythro-pentofuranosyl)-5-methyluracil

Downstream raw materials:

stavudin

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