O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine

Base Information

• Chemical Name: O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine
• CAS No.: 175400-30-3
• Molecular Formula: C₅₈H₆₆ClN₇O₈Si
• Molecular Weight: 1052.74

Synonyms:O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine

Chemical Property of O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine

Chemical Property:

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Technology Process of O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine

There total 5 articles about O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine 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: 65.0%

6-chloro-2-methoxy-9-<(5-hydroxypentyl)amino>acridine (95100-75-7) + O6-(2,4,6-triisopropylbenzenesulfonyl)-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N2-acetyldeoxyguanosine (175400-29-0) → O6<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N2-acetyldeoxyguanosine (175400-30-3)

Guidance literature:

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In acetonitrile; for 72h; Ambient temperature;

DOI:10.1016/0040-4020(95)01043-2

Reference yield:

2-(acetylamino)-9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one (4318-05-2) → O6<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N2-acetyldeoxyguanosine (175400-30-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / MeONa, MeOH / 0.08 h / 0 °C

2: 95 percent / pyridine / 1 h / Ambient temperature

3: 90 percent / imidazole, pyridine / 10 h / Ambient temperature

4: 90 percent / Et₃N, dimethylaminopyridine / acetonitrile; CH₂Cl₂ / 0 °C

5: 65 percent / DBU, pyridine, Et₃N / acetonitrile / 72 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; dmap; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/0040-4020(95)01043-2

Reference yield:

N2-acetyldeoxyguanosine (4318-06-3) → O6<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N2-acetyldeoxyguanosine (175400-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine / 1 h / Ambient temperature

2: 90 percent / imidazole, pyridine / 10 h / Ambient temperature

3: 90 percent / Et₃N, dimethylaminopyridine / acetonitrile; CH₂Cl₂ / 0 °C

4: 65 percent / DBU, pyridine, Et₃N / acetonitrile / 72 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/0040-4020(95)01043-2

upstream raw materials:

6-chloro-2-methoxy-9-<(5-hydroxypentyl)amino>acridine

O⁶-(2,4,6-triisopropylbenzenesulfonyl)-5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-N²-acetyldeoxyguanosine

2-(acetylamino)-9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one

N²-acetyldeoxyguanosine

Downstream raw materials:

O⁶<2-methoxy-6-chloro-9-(ω-pentylamino)>-acridine-5'-O-dimethoxytrityl-N²-acetyldeoxyguanosine

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