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

Base Information

• Chemical Name: ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate
• CAS No.: 1094603-23-2
• Molecular Formula: C₂₄H₂₂N₂O₇
• Molecular Weight: 450.448
• Mol file: 1094603-23-2.mol

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

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

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-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: 99.0%

sodium benzoate (532-32-1) + ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate (1094603-22-1) → ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate (1094603-23-2)

Guidance literature:

In dimethyl sulfoxide; at 100 ℃; for 5h;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose (293751-03-8) → ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate (1094603-23-2)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 3 h / Reflux; Inert atmosphere

2.1: sodium hydroxide / methanol; water; tetrahydrofuran / 1 h / 20 °C

3.1: dimethyl sulfoxide / 5 h / 100 °C

With N,O-bis-(trimethylsilyl)-acetamide; sodium hydroxide; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

(2R,3R,4S)-4-(benzyloxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate (1094603-21-0) → ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate (1094603-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / methanol; water; tetrahydrofuran / 1 h / 20 °C

2: dimethyl sulfoxide / 5 h / 100 °C

With sodium hydroxide; In tetrahydrofuran; methanol; water; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2014.04.050

upstream raw materials:

sodium benzoate

((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

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

Downstream raw materials:

1-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione

1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione