2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N⁶-benzoyl-5'-deoxyadenosine

Base Information

• Chemical Name: 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N⁶-benzoyl-5'-deoxyadenosine
• CAS No.: 305839-06-9
• Molecular Formula: C₄₃H₄₄N₈O₁₂
• Molecular Weight: 864.869

Synonyms:2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N⁶-benzoyl-5'-deoxyadenosine

Chemical Property of 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N⁶-benzoyl-5'-deoxyadenosine

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N⁶-benzoyl-5'-deoxyadenosine

There total 5 articles about 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N⁶-benzoyl-5'-deoxyadenosine 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: 68.0%

N-benzoyladenine (4005-49-6) + 1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-azido-5-deoxy-D-ribofuranoside → 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N6-benzoyl-5'-deoxyadenosine (305839-06-9)

Guidance literature:

N-benzoyladenine; With 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; for 7h; Heating;

1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-azido-5-deoxy-D-ribofuranoside; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 16h; Heating;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

Reference yield:

(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside (197644-81-8) → 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N6-benzoyl-5'-deoxyadenosine (305839-06-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2.02 g / TBAF / tetrahydrofuran; dioxane / 8 h / 50 °C

2.1: 1.22 g / PPh₃; DEAD; (PhO)2P(O)N₃ / tetrahydrofuran / 16 h / 20 °C

3.1: AcOH; H₂O / ethane-1,2-diol / 1 h / Heating

4.1: pyridine / 4 h / 20 °C

5.1: 1,1,1,3,3,3-hexamethyldisilazane / pyridine / 7 h / Heating

5.2: 68 percent / TMSOTf / 1,2-dichloro-ethane / 16 h / Heating

With pyridine; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; acetic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; pyridine; ethylene glycol; 1.1: Desilylation / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Acetylation / 5.1: Silylation / 5.2: Vorbrueggen-type condensation;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

Reference yield:

3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose (295320-98-8) → 2'-O-acetyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-azido-N6-benzoyl-5'-deoxyadenosine (305839-06-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.22 g / PPh₃; DEAD; (PhO)2P(O)N₃ / tetrahydrofuran / 16 h / 20 °C

2.1: AcOH; H₂O / ethane-1,2-diol / 1 h / Heating

3.1: pyridine / 4 h / 20 °C

4.1: 1,1,1,3,3,3-hexamethyldisilazane / pyridine / 7 h / Heating

4.2: 68 percent / TMSOTf / 1,2-dichloro-ethane / 16 h / Heating

With pyridine; diphenyl phosphoryl azide; water; acetic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; diethylazodicarboxylate; In tetrahydrofuran; pyridine; ethylene glycol; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Acetylation / 4.1: Silylation / 4.2: Vorbrueggen-type condensation;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

upstream raw materials:

N-benzoyladenine

3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

5-azido-5-deoxy-3-O-{2,6-di-O-benzyl-3,4-di-O-[(2'S,3'S)-2',3'-dimethoxybutane-2',3'-diyl]-α-D-glucopyranosyl}-1,2-O-isopropylidene-α-D-ribofuranoside

Downstream raw materials:

5'-azido-N⁶-benzoyl-3'-O-(2'',6''-di-O-benzyl-α-D-glucopyranosyl)-5'-deoxyadenosine

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