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

Base Information

• Chemical Name: (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate
• CAS No.: 293751-17-4
• Molecular Formula: C₂₃H₂₉N₃O₁₂S₂
• Molecular Weight: 603.628
• Mol file: 293751-17-4.mol

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

Chemical Property of (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate

There total 7 articles about (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate 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: 96.0%

4-N-Acetylcytosine (14631-20-0) + 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose (293751-03-8) → (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate (293751-17-4)

Guidance literature:

4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 1h; Reflux;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 5.5h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate (293751-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / pyridine / 1 h / 20 °C

2.1: 97 percent / conc. H₂SO₄ / acetic acid / 24 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

3.2: 82 percent / trimethylsilyl triflate / acetonitrile / 3 h / Heating

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; In acetic acid; acetonitrile;

DOI:10.1021/jo010732p

Reference yield:

3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (293751-01-6) → (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate (293751-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / conc. H₂SO₄ / acetic acid / 24 h / 20 °C

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

2.2: 82 percent / trimethylsilyl triflate / acetonitrile / 3 h / Heating

With N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; In acetic acid; acetonitrile;

DOI:10.1021/jo010732p

upstream raw materials:

4-N-Acetylcytosine

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

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:

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

((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

(1R,3R,4R,7S)-1-benzoyloxymethyl-7-benzyloxy-3-(cytosin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane