Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester
• CAS No.: 293751-31-2
• Molecular Formula: C₁₇H₁₆N₂O₇
• Molecular Weight: 360.323
• Mol file: 293751-31-2.mol

Synonyms:Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

Chemical Property of Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

There total 7 articles about Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester 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: 95.0%

sodium benzoate (532-32-1) + Toluene-4-sulfonic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester (314080-71-2) → Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester (293751-31-2)

Guidance literature:

In N,N-dimethyl-formamide; at 90 ℃; for 3h;

DOI:10.1016/S0960-894X(00)00434-0

Reference yield: 56.0%

C30H26N2O7 (293751-29-8) → Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester (293751-31-2)

Guidance literature:

C₃₀H₂₆N₂O₇; With iron(III) chloride; In dichloromethane; at 20 ℃; for 2.5h;

With water; In dichloromethane;

Reference yield:

1-(6,6-bis-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione → Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester (293751-31-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / DMAP / CH₂Cl₂ / 6 h / 20 °C

2: 97 percent / K₂CO₃ / dimethylformamide / 20 °C

3: 100 percent / 80 percent aq. AcOH / 6 h / Heating

4: NaH / dimethylformamide / 1 h / 20 °C

5: 95 percent / aq. cerium ammonium nitrate / acetonitrile / 18 h / 20 °C

6: 95 percent / dimethylformamide / 3 h / 90 °C

With dmap; ammonium cerium(IV) nitrate; sodium hydride; potassium carbonate; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Tosylation / 2: Alkylation / 3: Hydrolysis / 4: Cyclization / 5: oxidative cleavage / 6: Substitution;

DOI:10.1016/S0960-894X(00)00434-0

upstream raw materials:

sodium benzoate

Toluene-4-sulfonic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

Toluene-4-sulfonic acid (1R,3R,4R,7S)-7-hydroxy-3-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

C₂₇H₃₀N₂O₁₁S₂

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-methyleneuridine

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