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

Base Information

Chemical Name:2-amino-9-((1S,3R,4R,7R)-7-(benzyloxy)-1-(hydroxymethyl)-4-methyl-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one
CAS No.:1608456-18-3
Molecular Formula:C₁₉H₂₁N₅O₅
Molecular Weight:399.406
Hs Code.:

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

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

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

There total 15 articles about 2-amino-9-((1S,3R,4R,7R)-7-(benzyloxy)-1-(hydroxymethyl)-4-methyl-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one 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: 87.0%

: 1608456-17-2
((1R,3R,4R,7R)-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-7-(benzyloxy)-4-methyl-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

: 1608456-18-3
2-amino-9-((1S,3R,4R,7R)-7-(benzyloxy)-1-(hydroxymethyl)-4-methyl-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Guidance literature:: With ammonia; In methanol; at 20 ℃; for 18h; Sealed tube;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 2595-05-3
Diacetone D-glucose

: 1608456-18-3
2-amino-9-((1S,3R,4R,7R)-7-(benzyloxy)-1-(hydroxymethyl)-4-methyl-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere

1.2: 4.5 h / 0 °C

2.1: acetic acid / water / 72 h / 20 °C

3.1: pyridine / acetonitrile / 0 - 60 °C

4.1: hydrogenchloride / 1,4-dioxane / 96 h / 20 °C

5.1: titanium tetrachloride / dichloromethane / 35 °C

6.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 - 20 °C / Inert atmosphere

6.3: 2 h / -78 °C / Inert atmosphere

7.1: ammonia / methanol / 18 h / 20 °C

8.1: sodium periodate / water / 0.5 h / 0 °C

9.1: water; sodium hydroxide / 1,4-dioxane / 120 h / 0 - 20 °C

10.1: pyridine / 18 h / 0 - 20 °C

11.1: sulfuric acid; acetic acid / 72 h / 0 - 20 °C

12.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / Reflux

12.2: 3 h / Reflux; Inert atmosphere

13.1: 3-Hydroxypropionitrile; sodium hydride / mineral oil; tetrahydrofuran / 18 h / 0 - 20 °C

14.1: dimethyl sulfoxide / 4 h / 100 °C

15.1: ammonia / methanol / 18 h / 20 °C / Sealed tube

With pyridine; hydrogenchloride; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; water; titanium tetrachloride; sodium hydride; acetic acid; dimethyl sulfoxide; 3-Hydroxypropionitrile; trifluoroacetic anhydride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile; mineral oil; 6.3: |Grignard Reaction;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 22331-21-1
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

: 1608456-18-3
2-amino-9-((1S,3R,4R,7R)-7-(benzyloxy)-1-(hydroxymethyl)-4-methyl-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: acetic acid / water / 72 h / 20 °C

2.1: pyridine / acetonitrile / 0 - 60 °C

3.1: hydrogenchloride / 1,4-dioxane / 96 h / 20 °C

4.1: titanium tetrachloride / dichloromethane / 35 °C

5.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 - 20 °C / Inert atmosphere

5.3: 2 h / -78 °C / Inert atmosphere

6.1: ammonia / methanol / 18 h / 20 °C

7.1: sodium periodate / water / 0.5 h / 0 °C

8.1: water; sodium hydroxide / 1,4-dioxane / 120 h / 0 - 20 °C

9.1: pyridine / 18 h / 0 - 20 °C

10.1: sulfuric acid; acetic acid / 72 h / 0 - 20 °C

11.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / Reflux

11.2: 3 h / Reflux; Inert atmosphere

12.1: 3-Hydroxypropionitrile; sodium hydride / mineral oil; tetrahydrofuran / 18 h / 0 - 20 °C

13.1: dimethyl sulfoxide / 4 h / 100 °C

14.1: ammonia / methanol / 18 h / 20 °C / Sealed tube

With pyridine; hydrogenchloride; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; water; titanium tetrachloride; sodium hydride; acetic acid; dimethyl sulfoxide; 3-Hydroxypropionitrile; trifluoroacetic anhydride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile; mineral oil; 5.3: |Grignard Reaction;
DOI:10.1016/j.bmcl.2014.04.050