N⁴-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine

Base Information

• Chemical Name: N⁴-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine
• CAS No.: 619276-11-8
• Molecular Formula: C₃₈H₃₁N₃O₉
• Molecular Weight: 673.679

Synonyms:N⁴-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine

Chemical Property of N⁴-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine

There total 7 articles about N⁴-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine 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: 83.0%

benzoyl chloride (98-88-4) + N4-benzoyl-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine (619275-96-6) → N4-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine (619276-11-8)

Guidance literature:

In pyridine; at 4 ℃; for 0.5h;

DOI:10.1002/hlca.200390118

Reference yield:

4-N-benzoylcytosine (26661-13-2) → N4-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine (619276-11-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BSA / acetonitrile / 0.5 h / 80 °C

1.2: 82 percent / SnCl₄ / acetonitrile / 0.5 h / 80 °C

2.1: 82 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0.75 h / 4 °C

3.1: 89 percent / TsOH*H₂O / dimethylformamide / 20 °C

4.1: 82 percent / pyridine; CH₂Cl₂ / 0.5 h / 4 °C

5.1: 95 percent / TFA / methanol; tetrahydrofuran / 2 h / 20 °C

6.1: 83 percent / pyridine / 0.5 h / 4 °C

With benzenesulfonamide; sodium hydroxide; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200390118

Reference yield:

1-(α-L-arabinopyranosyl)-N4-benzoyl-cytosine (619275-56-8) → N4-benzoyl-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine (619276-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / TsOH*H₂O / dimethylformamide / 20 °C

2: 82 percent / pyridine; CH₂Cl₂ / 0.5 h / 4 °C

3: 95 percent / TFA / methanol; tetrahydrofuran / 2 h / 20 °C

4: 83 percent / pyridine / 0.5 h / 4 °C

With toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390118

upstream raw materials:

benzoyl chloride

N⁴-benzoyl-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)cytosine

4-N-benzoylcytosine

1-(α-L-arabinopyranosyl)-N⁴-benzoyl-cytosine

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