9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine

Base Information

• Chemical Name: 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine
• CAS No.: 619276-15-2
• Molecular Formula: C₃₆H₃₃N₅O₉
• Molecular Weight: 679.686

Synonyms:9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine

Chemical Property of 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine

Chemical Property:

Purity/Quality:

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Technology Process of 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine

There total 7 articles about 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine 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%

benzoyl chloride (98-88-4) + 9-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N2-isobutyrylguanine (619275-99-9) → 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N2-isobutyrylguanine (619276-15-2)

Guidance literature:

In pyridine; dichloromethane; at -20 ℃; for 3h;

DOI:10.1002/hlca.200390118

Reference yield:

2-N-isobutyrylguanine (21047-89-2) → 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N2-isobutyrylguanine (619276-15-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BSA / acetonitrile / 2 h / Heating

1.2: 44 percent / TMS-Tf / acetonitrile / 6 h / Heating

2.1: 80 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0.25 h / cooling

3.1: 87 percent / TsOH*H₂O / dimethylformamide / 20 °C

4.1: 88 percent / pyridine; CH₂Cl₂ / 0.5 h / 4 °C

5.1: 100 percent / acetic acid; H₂O / 10 h / 55 °C

6.1: 82 percent / pyridine; CH₂Cl₂ / 3 h / -20 °C

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

DOI:10.1002/hlca.200390118

Reference yield:

9-(α-L-arabinopyranosyl)-N2-isobutyryl-guanine (619275-60-4) → 9-(3'-O-benzoyl-2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N2-isobutyrylguanine (619276-15-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / TsOH*H₂O / dimethylformamide / 20 °C

2: 88 percent / pyridine; CH₂Cl₂ / 0.5 h / 4 °C

3: 100 percent / acetic acid; H₂O / 10 h / 55 °C

4: 82 percent / pyridine; CH₂Cl₂ / 3 h / -20 °C

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

DOI:10.1002/hlca.200390118

upstream raw materials:

benzoyl chloride

9-(2'-O-{[(9H-fluoren-9-yl)methoxy]carbonyl}-α-L-arabinopyranosyl)-N²-isobutyrylguanine

2-N-isobutyrylguanine

9-(α-L-arabinopyranosyl)-N²-isobutyryl-guanine

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