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

Base Information

Chemical Name:((1R,3R,4R,7S)-3-(4-amino-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methylmethanesulfonate
CAS No.:1610605-73-6
Molecular Formula:C₂₀H₂₃N₃O₈S
Molecular Weight:465.484
Hs Code.:

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

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

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

There total 8 articles about ((1R,3R,4R,7S)-3-(4-amino-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methylmethanesulfonate 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: 92.0%

: 293751-17-4
(2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate

: 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

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 18h;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetic acid; 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

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

Guidance literature:: Multi-step reaction with 3 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

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