N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin

Base Information

• Chemical Name: N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin
• CAS No.: 145594-14-5
• Molecular Formula: C₄₉H₄₄N₆O₁₁
• Molecular Weight: 892.922

Synonyms:

Chemical Property of N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin

There total 9 articles about N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin 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:

(+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate (145593-73-3) → N6-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin (145594-14-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 35 percent / 1a) hexamethyldisilazane, 1b) chlorotrimethylsilane, 2) SnCl₄ / acetonitrile / 20 h / Ambient temperature

2: 85 percent / 2N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

3: 89 percent / pyridine / (Bu₄N)ClO₄ / 1.33 h / Ambient temperature

4: 4-(dimethylamino)pyridine, pyridine / 20 h / Ambient temperature

5: pyridine, N,N'-dicyclohexylcarbodiimide / dioxane / 3 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; chloro-trimethyl-silane; tin(IV) chloride; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; tetrabutylammonium perchlorate; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1002/hlca.19920750503

Reference yield:

methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside (23339-18-6) → N6-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin (145594-14-5)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / r.t.

2: 35 percent / 1a) hexamethyldisilazane, 1b) chlorotrimethylsilane, 2) SnCl₄ / acetonitrile / 20 h / Ambient temperature

3: 85 percent / 2N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

4: 89 percent / pyridine / (Bu₄N)ClO₄ / 1.33 h / Ambient temperature

5: 4-(dimethylamino)pyridine, pyridine / 20 h / Ambient temperature

6: pyridine, N,N'-dicyclohexylcarbodiimide / dioxane / 3 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; chloro-trimethyl-silane; tin(IV) chloride; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; tetrabutylammonium perchlorate; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1002/hlca.19920750503

Reference yield:

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside (3427-20-1) → N6-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin (145594-14-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / H₂, AcOH / 10percent Pd/C / methanol / 8 h / Ambient temperature

2: Amberlit IRA 400 (OH^--Form) / methanol / 2 h / Ambient temperature

3: pyridine / r.t.

4: 35 percent / 1a) hexamethyldisilazane, 1b) chlorotrimethylsilane, 2) SnCl₄ / acetonitrile / 20 h / Ambient temperature

5: 85 percent / 2N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

6: 89 percent / pyridine / (Bu₄N)ClO₄ / 1.33 h / Ambient temperature

7: 4-(dimethylamino)pyridine, pyridine / 20 h / Ambient temperature

8: pyridine, N,N'-dicyclohexylcarbodiimide / dioxane / 3 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; chloro-trimethyl-silane; hydrogen; tin(IV) chloride; acetic acid; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; Amberlit IRA 400 (OH^--Form); tetrabutylammonium perchlorate; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1002/hlca.19920750503

upstream raw materials:

(+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate

methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside

4,4'-dimethoxytrityl chloride

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