9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine

Base Information

• Chemical Name: 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine
• CAS No.: 912567-51-2
• Molecular Formula: C₃₇H₄₁N₅O₈
• Molecular Weight: 683.761

Synonyms:9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine

Chemical Property of 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine

There total 11 articles about 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-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: 96.0%

N6-benzoyl-9-[5-benzyl-5-deoxy-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-2-O-isobutyryl-β-D-ribofuranosyl]adenine (912567-49-8) → 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine (912567-51-2)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1021/jm060310d

Reference yield:

2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside (518332-41-7) → 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine (912567-51-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

3.1: tetrahydrofuran / 20 °C

4.1: PhOCSCl; DMAP / acetonitrile / 20 °C

4.2: 18 percent / Bu₃SnH; AIBN / toluene / Heating

5.1: aq. TFA / 20 °C

6.1: Et₃N; DMAP / acetonitrile / 20 °C

7.1: hexamethyldisilazane; pyridine

7.2: 67 percent / SnCl₄ / acetonitrile / 20 °C

8.1: 96 percent / NaOMe / methanol / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; phenylcarbonochloridothioate; In tetrahydrofuran; methanol; diethyl ether; acetonitrile; 3.1: Moffatt oxidation / 5.2: Barton deoxygenation / 8.2: Vorbrueggen glycosylation;

DOI:10.1021/jm060310d

Reference yield:

1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside (196868-07-2) → 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribo-pentofuranosyl]adenine (912567-51-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

3.1: tetrahydrofuran / 20 °C

4.1: PhOCSCl; DMAP / acetonitrile / 20 °C

4.2: 18 percent / Bu₃SnH; AIBN / toluene / Heating

5.1: aq. TFA / 20 °C

6.1: Et₃N; DMAP / acetonitrile / 20 °C

7.1: hexamethyldisilazane; pyridine

7.2: 67 percent / SnCl₄ / acetonitrile / 20 °C

8.1: 96 percent / NaOMe / methanol / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; phenylcarbonochloridothioate; In tetrahydrofuran; methanol; diethyl ether; acetonitrile; 3.1: Moffatt oxidation / 5.2: Barton deoxygenation / 8.2: Vorbrueggen glycosylation;

DOI:10.1021/jm060310d

upstream raw materials:

N⁶-benzoyl-9-[5-benzyl-5-deoxy-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-2-O-isobutyryl-β-D-ribofuranosyl]adenine

2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside

5-O-tert-butyldimethylsilyl-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

5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

Downstream raw materials:

C₆₁H₆₂N₅O₁₇P₃

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