N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine
• CAS No.: 289044-89-9
• Molecular Formula: C₂₄H₃₁N₅O₄Si
• Molecular Weight: 481.627

Synonyms:N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine

Chemical Property of N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine

There total 6 articles about N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)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: 84.0%

N6-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-5-O-trityl-β-D-erythro-pentofuranosyl)adenine (289044-88-8) → N6-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine (289044-89-9)

Guidance literature:

With trifluoroacetic acid; In chloroform; water; at 20 ℃; for 0.25h;

DOI:10.1021/jo0001333

Reference yield:

5'-O-(triphenylmethyl)adenosine (18048-85-6) → N6-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine (289044-89-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 66 percent / AgNO₃; pyridine / tetrahydrofuran / 15 h / 20 °C

2: 16 g / CrO₃; pyridine; further reagents / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 9.2 g / tetrahydrofuran / -78 - 0 °C

4: 95 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 20 °C

5: 84 percent / trifluoroacetic acid / CHCl₃; H₂O / 0.25 h / 20 °C

With pyridine; chromium(VI) oxide; dmap; silver nitrate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; water; 1: Substitution / 2: Oxidation / 3: Substitution / 4: Acylation / 5: Hydrolysis;

DOI:10.1021/jo0001333

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N6-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine (289044-89-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 66 percent / AgNO₃; pyridine / tetrahydrofuran / 15 h / 20 °C

2: 16 g / CrO₃; pyridine; further reagents / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 9.2 g / tetrahydrofuran / -78 - 0 °C

4: 95 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 20 °C

5: 84 percent / trifluoroacetic acid / CHCl₃; H₂O / 0.25 h / 20 °C

With pyridine; chromium(VI) oxide; dmap; silver nitrate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; water; 1: Substitution / 2: Oxidation / 3: Substitution / 4: Acylation / 5: Hydrolysis;

DOI:10.1021/jo0001333

upstream raw materials:

N⁶-benzoyl-9-(2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-5-O-trityl-β-D-erythro-pentofuranosyl)adenine

5'-O-(triphenylmethyl)adenosine

tert-butyldimethylsilyl chloride

2'-O-TBS-5'-O-trityl-3'-ketoadenosine

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