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

Base Information

• Chemical Name: 1-<2'-O,3'-O-Cyclopentyl-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N³-(4-methoxybenzyl)-5-methyluracil
• CAS No.: 161824-97-1
• Molecular Formula: C₃₁H₃₆N₂O₈
• Molecular Weight: 564.635

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

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

Chemical Property:

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

There total 4 articles about 1-<2'-O,3'-O-Cyclopentyl-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N³-(4-methoxybenzyl)-5-methyluracil 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: 75.0%

p-Methoxybenzyl bromide (2746-25-0) + 1-(2'-O,3'-O-Cyclopentyl-5'-hydroxy-β-D-erythro-pentofuranosyl)-5-methyluracil (161824-82-4) → 1-<2'-O,3'-O-Cyclopentyl-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N3-(4-methoxybenzyl)-5-methyluracil (161824-97-1)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; 1.) r.t., 20 min, 2.) 65 deg C, 18 h;

DOI:10.1021/jo00103a017

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 1-<2'-O,3'-O-Cyclopentyl-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N3-(4-methoxybenzyl)-5-methyluracil (161824-97-1)

Guidance literature:

Multi-step reaction with 4 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

With t-butyldimethylsiyl triflate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; 1,2-dimethoxyethane; 1,2-dichloro-ethane;

DOI:10.1021/jo00103a017

Reference yield:

2',3',5'-tri-O-benzoyluridine (3180-76-5) → 1-<2'-O,3'-O-Cyclopentyl-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N3-(4-methoxybenzyl)-5-methyluracil (161824-97-1)

Guidance literature:

Multi-step reaction with 3 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

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; 1,2-dimethoxyethane; 1,2-dichloro-ethane;

DOI:10.1021/jo00103a017

upstream raw materials:

p-Methoxybenzyl bromide

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

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

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

Downstream raw materials:

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

stavudin

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

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