((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

Base Information

Chemical Name:((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate
CAS No.:1610605-66-7
Molecular Formula:C₂₆H₂₅N₃O₇
Molecular Weight:491.5
Hs Code.:

Synonyms:((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

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Chemical Property of ((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

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Technology Process of ((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

There total 9 articles about ((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate 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: 58.0%

: 532-32-1
sodium benzoate

: 1610605-73-6
((1R,3R,4R,7S)-3-(4-amino-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methylmethanesulfonate

: 1610605-66-7
((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

Guidance literature:: In dimethyl sulfoxide; at 100 ℃; for 12h;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose

: 1610605-66-7
((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C

2.1: pyridine / 1 h / 20 °C

3.1: sulfuric acid / acetic acid / 20 °C

4.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / Reflux

4.2: 5.5 h / Reflux; Inert atmosphere

5.1: sodium hydroxide / methanol; tetrahydrofuran / 18 h / 20 °C

6.1: dimethyl sulfoxide / 12 h / 100 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetic acid; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 293751-01-6
3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 1610605-66-7
((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfuric acid / acetic acid / 20 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / Reflux

2.2: 5.5 h / Reflux; Inert atmosphere

3.1: sodium hydroxide / methanol; tetrahydrofuran / 18 h / 20 °C

4.1: dimethyl sulfoxide / 12 h / 100 °C

With N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; sodium hydroxide; In tetrahydrofuran; methanol; acetic acid; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/j.bmcl.2014.04.050