9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine

Base Information

• Chemical Name: 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine
• CAS No.: 619277-27-9
• Molecular Formula: C₄₆H₄₁N₅O₁₀
• Molecular Weight: 823.859

Synonyms:9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine

Chemical Property of 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine

Chemical Property:

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Technology Process of 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine

There total 12 articles about 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine 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: 41.0%

9-{4'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N2-(phenoxyacetyl)guanine (619277-11-1) → 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N2-(phenoxyacetyl)guanine (619277-27-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1002/hlca.200390118

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N2-(phenoxyacetyl)guanine (619277-27-9)

Guidance literature:

Multi-step reaction with 4 steps

1: collodine / CH₂Cl₂ / 6 h / 20 °C

2: 18.3 g / NaHCO₃; citric acid / H₂O; CH₂Cl₂

3: 80.7 percent / 4-DMAP / CH₂Cl₂; pyridine / 15 h / 20 °C

4: 41 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

With dmap; collodine; sodium hydrogencarbonate; triethylamine; citric acid; In pyridine; dichloromethane; water;

DOI:10.1002/hlca.200390118

Reference yield:

2-N-isobutyrylguanine (21047-89-2) → 9-{3'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N2-(phenoxyacetyl)guanine (619277-27-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: BSA / acetonitrile / 2 h / Heating

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

2.1: 95 percent / NH₃ / methanol / 48 h / 20 °C

3.1: pyridine / 0.5 h / 20 °C

4.1: 1-HOBT / pyridine; CH₂Cl₂ / 20 °C

5.1: 10.6 g / H₂O

6.1: pyridine; dimethylformamide / 1 h / 0 °C

7.1: collodine / CH₂Cl₂ / 6 h / 20 °C

8.1: 18.3 g / NaHCO₃; citric acid / H₂O; CH₂Cl₂

9.1: 80.7 percent / 4-DMAP / CH₂Cl₂; pyridine / 15 h / 20 °C

10.1: 41 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

With benzenesulfonamide; dmap; collodine; ammonia; water; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; citric acid; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200390118

upstream raw materials:

9-{4'-O-benzoyl-2'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-arabinopyranosyl}-N²-(phenoxyacetyl)guanine

4,4'-dimethoxytrityl chloride

2-N-isobutyrylguanine

9-(α-L-arabinopyranosyl)guanine

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