6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine

Base Information

• Chemical Name: 6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine
• CAS No.: 672956-48-8
• Molecular Formula: C₄₂H₃₅N₅O₉
• Molecular Weight: 753.768

Synonyms:6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine

Chemical Property of 6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine

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Technology Process of 6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine

There total 7 articles about 6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine 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: 72.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + benzoyl chloride (98-88-4) + 6-amino-N6-benzoyl-2-[(prop-2-enyl)oxy]-9-(β-D-ribopyranosyl)purine (672955-47-4) → 6-amino-N6,N6-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine (672956-48-8)

Guidance literature:

p-Anisaldehyde dimethyl acetal; 6-amino-N⁶-benzoyl-2-[(prop-2-enyl)oxy]-9-(β-D-ribopyranosyl)purine; With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 2h;

benzoyl chloride; In pyridine; at 0 - 20 ℃;

DOI:10.1002/hlca.200390349

Reference yield:

benzoyl chloride (98-88-4) → 6-amino-N6,N6-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine (672956-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 0 - 20 °C

1.2: 1.12 g / NaOH; water / tetrahydrofuran; methanol / 0.5 h / 0 °C

2.1: TsOH / dimethylformamide / 2 h / 60 °C

2.2: 72 percent / pyridine / 0 - 20 °C

With pyridine; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390349

Reference yield:

6-amino-2-chloro-9-(β-D-ribopyranosyl)purine (16755-02-5) → 6-amino-N6,N6-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine (672956-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Cs₂CO₃; 3A MS / 6 h / 90 °C

2.1: pyridine / 0 - 20 °C

2.2: 1.12 g / NaOH; water / tetrahydrofuran; methanol / 0.5 h / 0 °C

3.1: TsOH / dimethylformamide / 2 h / 60 °C

3.2: 72 percent / pyridine / 0 - 20 °C

With pyridine; caesium carbonate; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390349

upstream raw materials:

p-Anisaldehyde dimethyl acetal

benzoyl chloride

6-amino-N⁶-benzoyl-2-[(prop-2-enyl)oxy]-9-(β-D-ribopyranosyl)purine

6-amino-2-chloro-9-(β-D-ribopyranosyl)purine

Downstream raw materials:

Benzoic acid (2R,3R,4R,5R)-2-(2-allyloxy-6-dibenzoylamino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-4-hydroxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3R,4S,5R)-2-(2-allyloxy-6-benzoylamino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-3-hydroxy-tetrahydro-pyran-4-yl ester

6-amino-N⁶,N⁶-dibenzoyl-9-(2'-O-benzoyl-β-D-ribopyranosyl)-2-[(prop-2-enyl)oxy]purine

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