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

Base Information

• Chemical Name: 9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N₂-octyl-9H-purine-2,6-diamine
• CAS No.: 1341074-94-9
• Molecular Formula: C₄₂H₅₄N₆O₄Si
• Molecular Weight: 735.014

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

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

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

There total 3 articles about 9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N₂-octyl-9H-purine-2,6-diamine 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: 29.0%

Octanal (124-13-0) + 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 (1341074-87-0) → 9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N2-octyl-9H-purine-2,6-diamine (1341074-94-9)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 25 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.07.022

Reference yield:

2,6-diaminopurine (1904-98-9) → 9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N2-octyl-9H-purine-2,6-diamine (1341074-94-9)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1016/j.bmc.2011.07.022

Reference yield:

(2R,3R,4S,5S)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(2,6-diamino-9H-purin-9-yl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate (1341074-82-5) → 9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-N2-octyl-9H-purine-2,6-diamine (1341074-94-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium cyanoborohydride; sodium hydroxide; In tetrahydrofuran; methanol; water;

DOI:10.1016/j.bmc.2011.07.022

upstream raw materials:

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

Octanal

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

Downstream raw materials:

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

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