((1S,3R,4R,7S)-3-(6-amino-2-fluoro-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-fluoro-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol
CAS No.:1341074-25-6
Molecular Formula:C₁₈H₁₈FN₅O₄
Molecular Weight:387.37
Hs Code.:

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

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

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

There total 4 articles about ((1S,3R,4R,7S)-3-(6-amino-2-fluoro-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: 85.0%

: 1341075-12-4
9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-2-fluoro-9H-purin-6-amine

: 1341074-25-6
((1S,3R,4R,7S)-3-(6-amino-2-fluoro-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 25 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.07.022

Reference yield:

: 1341075-09-9
(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

: 1341074-25-6
((1S,3R,4R,7S)-3-(6-amino-2-fluoro-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydroxide / tetrahydrofuran; water / 15 h / 0 - 25 °C / Inert atmosphere

2: pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 0 - 25 °C / Inert atmosphere

With pyridine hydrogenfluoride; sodium hydroxide; In tetrahydrofuran; water;
DOI:10.1016/j.bmc.2011.07.022

Reference yield:

: 212970-74-6
Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

: 1341074-25-6
((1S,3R,4R,7S)-3-(6-amino-2-fluoro-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / 80 °C / Inert atmosphere

1.2: 3 h / 0 - 80 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: sodium hydroxide / tetrahydrofuran; water / 15 h / 0 - 25 °C / Inert atmosphere

3.1: pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 0 - 25 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; pyridine hydrogenfluoride; sodium hydroxide; In tetrahydrofuran; water; acetonitrile; 1.2: Vorbrüggen coupling;
DOI:10.1016/j.bmc.2011.07.022