N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine
• CAS No.: 289891-34-5
• Molecular Formula: C₄₄H₄₆BrN₅O₈
• Molecular Weight: 852.782

Synonyms:N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine

There total 6 articles about N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]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:

C58H54BrN5O10 → N6-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine (289891-34-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 4 ℃; for 0.25h;

DOI:10.1002/1522-2675(20000607)83:6<1127::AID-HLCA1127>3.0.CO;2-B

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N6-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine (289891-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: AgNO₃; sym-collidine / CH₂Cl₂ / 3 h / 20 °C

2: 10N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.25 h / 4 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; silver nitrate; In tetrahydrofuran; methanol; dichloromethane; water; 1: Alkylation / 2: debenzoylation;

DOI:10.1002/1522-2675(20000607)83:6<1127::AID-HLCA1127>3.0.CO;2-B

Reference yield:

N-benzoyladenine (4005-49-6) → N6-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]adenine (289891-34-5)

Guidance literature:

Multi-step reaction with 4 steps

1: bis(trimethylsilyl)acetamide (BSA); SnCl₄ / acetonitrile / 1.33 h / 60 °C

2: CF₃COOH / H₂O / 12 h / 20 °C

3: AgNO₃; sym-collidine / CH₂Cl₂ / 3 h / 20 °C

4: 10N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.25 h / 4 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; tin(IV) chloride; silver nitrate; bis-(trimethylsilyl)acetamide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: nucleosidation / 2: desilylation / 3: Alkylation / 4: debenzoylation;

DOI:10.1002/1522-2675(20000607)83:6<1127::AID-HLCA1127>3.0.CO;2-B

upstream raw materials:

4,4'-dimethoxytrityl chloride

N-benzoyladenine

N⁶-benzoyl-9-[2',3'-di-O-benzoyl-6'-O-(5-bromopentyl)-β-D-allofuranosyl]adenine

Downstream raw materials:

N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]adenine

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