6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

Base Information

Chemical Name:6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine
CAS No.:883740-55-4
Molecular Formula:C₄₄H₄₉N₅O₇Si
Molecular Weight:787.988
Hs Code.:

Synonyms:6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

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Chemical Property of 6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

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Technology Process of 6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

There total 13 articles about 6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine 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: 48.0%

: 883740-53-2
6-N-benzoyl-9-[5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 6-N-benzoyl-9-[3-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

: 883740-55-4
6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

Guidance literature:: With pyridine; 1H-imidazole; at 20 ℃; for 15h;
DOI:10.1016/j.tet.2005.12.007

Reference yield:

: 110237-79-1
5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose

: 883740-55-4
6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

Guidance literature:: Multi-step reaction with 9 steps

1.1: sulfuric acid; aq. AcOH / 1 h / 50 °C

1.2: 73 percent / pyridine / 6 h / 50 °C

2.1: 88 percent / SnCl₄ / acetonitrile / 4 h / 20 °C

3.1: 92 percent / NH₃ / methanol / 1.5 h / 0 °C

4.1: pyridine / CH₂Cl₂ / 1.5 h / -30 °C

5.1: 380 mg / 18-crown-6 / CH₂Cl₂; toluene / 16 h / 50 °C

6.1: 0.21 g / aq. NaOH; pyridine / ethanol / 0.5 h / 0 °C

7.1: 0.12 g / Pd/C; HCO₂NH₄ / ethanol / 2 h / Heating

8.1: 92 percent / pyridine / 12 h / 20 °C

9.1: 48 percent / imidazole; pyridine / 15 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; palladium on activated charcoal; 18-crown-6 ether; sulfuric acid; ammonia; ammonium formate; tin(IV) chloride; acetic acid; In methanol; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.tet.2005.12.007

Reference yield:

: 525596-21-8
1,2-di-O-acetyl-5-O-benzoyl-3-O-benzyl-L-arabinofuranose

: 883740-55-4
6-N-benzoyl-9-[2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]adenine

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / SnCl₄ / acetonitrile / 4 h / 20 °C

2: 92 percent / NH₃ / methanol / 1.5 h / 0 °C

3: pyridine / CH₂Cl₂ / 1.5 h / -30 °C

4: 380 mg / 18-crown-6 / CH₂Cl₂; toluene / 16 h / 50 °C

5: 0.21 g / aq. NaOH; pyridine / ethanol / 0.5 h / 0 °C

6: 0.12 g / Pd/C; HCO₂NH₄ / ethanol / 2 h / Heating

7: 92 percent / pyridine / 12 h / 20 °C

8: 48 percent / imidazole; pyridine / 15 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; palladium on activated charcoal; 18-crown-6 ether; ammonia; ammonium formate; tin(IV) chloride; In methanol; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.tet.2005.12.007