1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate

Base Information

• Chemical Name: 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate
• CAS No.: 1610460-04-2
• Molecular Formula: C₂₂H₂₉N₆O₆P
• Molecular Weight: 504.483

Synonyms:1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate

Chemical Property of 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate

Chemical Property:

Purity/Quality:

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Technology Process of 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate

There total 8 articles about 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate 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: 51.0%

phenyl(isopropoxy-L-alaninyl) phosphorochloridate (261909-49-3) + 5(R)-(6-amino-9H-purin-9-yl)tetrahydro-3(S)-furanmethanol (146609-00-9) → 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate (1610460-04-2)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; at 25 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jo500659e

Reference yield:

N-benzoyladenine (4005-49-6) → 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate (1610460-04-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; pyridine / Reflux; Inert atmosphere

1.2: 0.13 h / 0 - 150 °C / Inert atmosphere; Microwave irradiation

2.1: ammonia / methanol / 48 h / 25 °C / Inert atmosphere

3.1: formic acid; Pd(OH)2/C / methanol / 55 °C / Inert atmosphere

3.2: 3 h / 25 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 25 °C / Inert atmosphere

5.1: dmap; p-Tolyl chlorothionoformate / acetonitrile / 2 h / 25 °C / Inert atmosphere

5.2: 3 h / 110 - 120 °C / Inert atmosphere

6.1: ammonium fluoride / methanol / 48 h / 55 °C / Inert atmosphere

7.1: 1-methyl-1H-imidazole / tetrahydrofuran / 48 h / 25 °C / Inert atmosphere

With pyridine; 1H-imidazole; 1-methyl-1H-imidazole; dmap; ammonium fluoride; chloro-trimethyl-silane; formic acid; p-Tolyl chlorothionoformate; Pd(OH)2/C; ammonia; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; 1.2: |Vorbrueggen Nucleoside Synthesis / 5.1: |Barton-McCombie Deoxygenation / 5.2: |Barton-McCombie Deoxygenation;

DOI:10.1021/jo500659e

Reference yield:

1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-D-apio-D-furanose (1374011-55-8) → 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate (1610460-04-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; pyridine / Reflux; Inert atmosphere

1.2: 0.13 h / 0 - 150 °C / Inert atmosphere; Microwave irradiation

2.1: ammonia / methanol / 48 h / 25 °C / Inert atmosphere

3.1: formic acid; Pd(OH)2/C / methanol / 55 °C / Inert atmosphere

3.2: 3 h / 25 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 25 °C / Inert atmosphere

5.1: dmap; p-Tolyl chlorothionoformate / acetonitrile / 2 h / 25 °C / Inert atmosphere

5.2: 3 h / 110 - 120 °C / Inert atmosphere

6.1: ammonium fluoride / methanol / 48 h / 55 °C / Inert atmosphere

7.1: 1-methyl-1H-imidazole / tetrahydrofuran / 48 h / 25 °C / Inert atmosphere

With pyridine; 1H-imidazole; 1-methyl-1H-imidazole; dmap; ammonium fluoride; chloro-trimethyl-silane; formic acid; p-Tolyl chlorothionoformate; Pd(OH)2/C; ammonia; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; 1.2: |Vorbrueggen Nucleoside Synthesis / 5.1: |Barton-McCombie Deoxygenation / 5.2: |Barton-McCombie Deoxygenation;

DOI:10.1021/jo500659e

upstream raw materials:

N-benzoyladenine

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

5(R)-(6-amino-9H-purin-9-yl)tetrahydro-3(S)-furanmethanol

1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-D-apio-D-furanose

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