N⁶-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine
• CAS No.: 259746-24-2
• Molecular Formula: C₂₅H₂₇N₅O₇
• Molecular Weight: 509.519

Synonyms:N⁶-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine

Chemical Property of N⁶-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine

There total 5 articles about N⁶-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-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: 80.0%

N-benzoyladenine (4005-49-6) + 1,2-di-O-acetyl-3,6-anhydro-5-O-pivaloyl-α,β-D-glucofuranose → N6-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine (259746-24-2)

Guidance literature:

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 70 - 80 ℃; for 0.75h;

DOI:10.1016/S0040-4020(99)00911-4

Reference yield:

3-O-Acetyl-1,2-O-isopropyliden-D-glucofuranose-5,6-sulfit (94933-92-3) → N6-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine (259746-24-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / sodium methoxide / methanol / 0.5 h / 20 °C

2: 98 percent / pyridine; DMAP / 24 h / 20 °C

3: 83 percent / aq. AcOH / 4 h / 120 - 125 °C

4: 93 percent / pyridine / 20 °C

5: 80 percent / BSA / TMSOTf / 1,2-dichloro-ethane / 0.75 h / 70 - 80 °C

With pyridine; benzenesulfonamide; dmap; sodium methylate; acetic acid; trimethylsilyl trifluoromethanesulfonate; In methanol; 1,2-dichloro-ethane; 1: Cyclization / 2: Acylation / 3: Hydrolysis / 4: Acetylation / 5: Substitution;

DOI:10.1016/S0040-4020(99)00911-4

Reference yield:

3,6-Anhydro-1,2-O-isopropyliden-α-D-glucofuranose (27821-03-0) → N6-benzoyl-9-(2'-O-acetyl-3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine (259746-24-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyridine; DMAP / 24 h / 20 °C

2: 83 percent / aq. AcOH / 4 h / 120 - 125 °C

3: 93 percent / pyridine / 20 °C

4: 80 percent / BSA / TMSOTf / 1,2-dichloro-ethane / 0.75 h / 70 - 80 °C

With pyridine; benzenesulfonamide; dmap; acetic acid; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; 1: Acylation / 2: Hydrolysis / 3: Acetylation / 4: Substitution;

DOI:10.1016/S0040-4020(99)00911-4

upstream raw materials:

N-benzoyladenine

3-O-Acetyl-1,2-O-isopropyliden-D-glucofuranose-5,6-sulfit

3,6-Anhydro-1,2-O-isopropyliden-α-D-glucofuranose

3,6-anhydro-1,2-O-isopropylidene-5-O-pivaloyl-α-D-glucofuranose

Downstream raw materials:

N⁶-benzoyl-9-(3',6'-anhydro-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine

N⁶-benzoyl-9-(3',6'-anhydro-2'-deoxy-5'-O-pivaloyl-β-D-glucofuranosyl)-adenine

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