((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Base Information

• Chemical Name: ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol
• CAS No.: 1341074-04-1
• Molecular Formula: C₂₂H₂₈N₆O₄
• Molecular Weight: 440.502

Synonyms:((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Chemical Property of ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

There total 5 articles about ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol 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: 77.0%

9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N2-butyl-9H-purine-2,6-diamine (1341074-97-2) → ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol (1341074-04-1)

Guidance literature:

9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N₂-butyl-9H-purine-2,6-diamine; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 25 ℃; for 16h; Inert atmosphere;

With water; In tetrahydrofuran; at 25 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.07.022

Reference yield:

Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (212970-74-6) → ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol (1341074-04-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / 65 °C / Inert atmosphere

1.2: 3 h / 0 - 65 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: sodium hydroxide / tetrahydrofuran; water / 2 h / 0 - 25 °C / Inert atmosphere

3.1: sodium cyanoborohydride / methanol / 48 h / 25 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 - 25 °C / Inert atmosphere

4.2: 0.17 h / 25 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; sodium cyanoborohydride; sodium hydroxide; In tetrahydrofuran; methanol; water; acetonitrile; 1.2: Vorbrüggen coupling;

DOI:10.1016/j.bmc.2011.07.022

Reference yield:

2,6-diaminopurine (1904-98-9) → ((1S,3R,4R,7S)-3-(6-amino-2-(butylamino)-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol (1341074-04-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / 65 °C / Inert atmosphere

1.2: 3 h / 0 - 65 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: sodium hydroxide / tetrahydrofuran; water / 2 h / 0 - 25 °C / Inert atmosphere

3.1: sodium cyanoborohydride / methanol / 48 h / 25 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 - 25 °C / Inert atmosphere

4.2: 0.17 h / 25 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; sodium cyanoborohydride; sodium hydroxide; In tetrahydrofuran; methanol; water; acetonitrile; 1.2: Vorbrüggen coupling;

DOI:10.1016/j.bmc.2011.07.022

upstream raw materials:

9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N₂-butyl-9H-purine-2,6-diamine

(2R,3R,4S,5S)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(2,6-diamino-9H-purin-9-yl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-9H-purine-2,6-diamine

2,6-diaminopurine

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