N⁴-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine
• CAS No.: 619275-83-1
• Molecular Formula: C₃₉H₃₃N₃O₉
• Molecular Weight: 687.706

Synonyms:N⁴-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine

Chemical Property of N⁴-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine

There total 5 articles about N⁴-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-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: 82.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + N4-benzoyl-1-(3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine (619275-68-2) → N4-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine (619275-83-1)

Guidance literature:

In pyridine; dichloromethane; at 4 ℃; for 0.5h;

DOI:10.1002/hlca.200390118

Reference yield:

4-N-benzoylcytosine (26661-13-2) → N4-benzoyl-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine (619275-83-1)

Guidance literature:

Multi-step reaction with 4 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

With benzenesulfonamide; sodium hydroxide; toluene-4-sulfonic 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-1-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine (619275-83-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1002/hlca.200390118

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

N⁴-benzoyl-1-(3',4'-O-[(4-methoxyphenyl)methylidene]-α-L-arabinopyranosyl)cytosine

4-N-benzoylcytosine

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

Downstream raw materials:

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

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

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