N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide

Base Information

• Chemical Name: N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide
• CAS No.: 681811-47-2
• Molecular Formula: C₁₆H₁₇N₃O₅
• Molecular Weight: 331.328
• Mol file: 681811-47-2.mol

Synonyms:N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide

Chemical Property of N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide

There total 9 articles about N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide 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: 70.0%

acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester (681811-46-1) → N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide (681811-47-2)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane; at -5 ℃; for 0.666667h;

DOI:10.1016/j.bmc.2003.12.002

Reference yield:

(2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-ol (681811-42-7) → N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide (681811-47-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

2.1: ammonium sulfate; HMDS / 150 - 160 °C

2.2: 71 percent / TMSOTf / acetonitrile / 20 °C

3.1: BCl₃ / CH₂Cl₂ / 2 h / -78 °C

3.2: 52 percent / pyridine / 20 °C

4.1: 70 percent / K₂CO₃ / methanol; CH₂Cl₂ / 0.67 h / -5 °C

With pyridine; dmap; ammonium sulfate; boron trichloride; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2003.12.002

Reference yield:

(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (681811-41-6) → N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide (681811-47-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 75 percent / p-TsOH / 20 °C

2.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

3.1: ammonium sulfate; HMDS / 150 - 160 °C

3.2: 71 percent / TMSOTf / acetonitrile / 20 °C

4.1: BCl₃ / CH₂Cl₂ / 2 h / -78 °C

4.2: 52 percent / pyridine / 20 °C

5.1: 70 percent / K₂CO₃ / methanol; CH₂Cl₂ / 0.67 h / -5 °C

With pyridine; dmap; ammonium sulfate; boron trichloride; potassium carbonate; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2003.12.002

upstream raw materials:

acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

(2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-ol

acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester

(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole