N⁶-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine
• CAS No.: 222848-75-1
• Molecular Formula: C₄₀H₃₆ClN₅O₈
• Molecular Weight: 750.208

Synonyms:N⁶-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine

Chemical Property of N⁶-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine

There total 6 articles about N⁶-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine 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: 50.0%

Chloroacetic anhydride (541-88-8) + N6-benzoyl-9-{4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine (222848-69-3) → N6-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine (222848-75-1)

Guidance literature:

Chloroacetic anhydride; N⁶-benzoyl-9-{4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine; With pyridine; In dichloromethane; at 20 ℃; for 1h;

With triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1002/1522-2675(200202)85:2<399::AID-HLCA399>3.0.CO;2-2

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N6-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine (222848-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 40 percent / 4 Angstroem molecular sieves / pyridine / 20 °C

2.1: pyridine / CH₂Cl₂ / 1 h / 20 °C

2.2: 50 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

With pyridine; 4 A molecular sieve; In pyridine; dichloromethane;

DOI:10.1002/1522-2675(200202)85:2<399::AID-HLCA399>3.0.CO;2-2

Reference yield:

N-benzoyladenine (4005-49-6) → N6-benzoyl-9-{3'-O-(chloroacetyl)-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine (222848-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 78 percent / BSA; SnCl₄ / acetonitrile / 1.5 h / 60 °C

2.1: 91 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0.33 h / 4 °C

3.1: 40 percent / 4 Angstroem molecular sieves / pyridine / 20 °C

4.1: pyridine / CH₂Cl₂ / 1 h / 20 °C

4.2: 50 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

With pyridine; benzenesulfonamide; sodium hydroxide; 4 A molecular sieve; tin(IV) chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetonitrile;

DOI:10.1002/1522-2675(200202)85:2<399::AID-HLCA399>3.0.CO;2-2

upstream raw materials:

Chloroacetic anhydride

N⁶-benzoyl-9-{4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine

4,4'-dimethoxytrityl chloride

N-benzoyladenine

Downstream raw materials:

N⁶-benzoyl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}adenine

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