N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Base Information

Chemical Name:N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide
CAS No.:1610605-72-5
Molecular Formula:C₂₆H₂₅N₅O₆
Molecular Weight:503.514
Hs Code.:

Synonyms:N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

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Chemical Property of N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

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Technology Process of N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

There total 14 articles about N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide 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: 11.0%

: 1610605-69-0
N-(9-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

: 75-16-1
methylmagnesium bromide

: 1610605-72-5
N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

: 1610605-79-2
N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((R)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Guidance literature:: N-(9-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide; With acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; at -78 ℃; for 1h; Molecular sieve; Inert atmosphere;

With triethylamine; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h; Molecular sieve;

methylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 1h; Molecular sieve;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 293751-16-3
(1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

: 1610605-72-5
N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap / dichloromethane; pyridine / 72 h / 20 °C

2.1: pyridine / 18 h / 20 °C

3.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

4.1: acetic anhydride; dimethyl sulfoxide / tetrahydrofuran / 1 h / -78 °C / Molecular sieve; Inert atmosphere

4.2: 1.5 h / -78 - 20 °C / Molecular sieve

4.3: 1 h / 0 °C / Molecular sieve

With pyridine; hydrogenchloride; dmap; acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; 4.2: |Grignard Reaction;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 1610605-77-0
2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

: 1610605-72-5
N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / 18 h / 20 °C

2.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

3.1: acetic anhydride; dimethyl sulfoxide / tetrahydrofuran / 1 h / -78 °C / Molecular sieve; Inert atmosphere

3.2: 1.5 h / -78 - 20 °C / Molecular sieve

3.3: 1 h / 0 °C / Molecular sieve

With pyridine; hydrogenchloride; acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; 1,4-dioxane; 3.2: |Grignard Reaction;
DOI:10.1016/j.bmcl.2014.04.050