Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 259137-72-9
• Molecular Formula: C₁₆H₁₆N₂O₆
• Molecular Weight: 332.313
• Mol file: 259137-72-9.mol

Synonyms:Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 17 articles about Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-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: 69.0%

benzoyl chloride (98-88-4) + 1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol (64332-73-6) → Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (259137-72-9)

Guidance literature:

With pyridine; at -15 ℃; for 2h;

DOI:10.1080/07328319908044614

Reference yield:

1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9) → Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (259137-72-9)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

4: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

5: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

6: 93 percent / toluene / 2.5 h / 0 - 20 °C

7: 54 percent / aq. H₂SO₄ / dioxane / 2.5 h / 100 °C

8: 87 percent / NH₄F / methanol / 8 h / Heating

9: 69 percent / pyridine / 2 h / -15 °C

With pyridine; 1H-imidazole; ammonium fluoride; thionyl chloride; sodium azide; sulfuric acid; hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Cyclization / 3: Ring cleavage / 4: Substitution / 5: Reduction / 6: Addition / 7: Cyclization / 8: Substitution / 9: Acylation;

DOI:10.1080/07328319908044614

Reference yield:

methyl ribofuranoside (1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7) → Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (259137-72-9)

Guidance literature:

Multi-step reaction with 9 steps

1: HMDS / acetonitrile

2: 1.) TMSOTf, Et₃Si / 1.) MeCN, 2.) H₂O

3: 74 percent / pyridine / 1.) -15 deg C, 5 h, 2.) room temperature, overnight

4: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

5: 84 percent / NaN₃ / dimethylformamide / 3.5 h / 100 °C

6: H₂ / Pd/C / aq. ethanol / 3 h / 2068.6 Torr / Ambient temperature

7: 92 percent / dimethylformamide; toluene / 16 h / 0 deg C -> room temperature

8: 91 percent / H₂SO₄ / dioxane / 3.5 h / Heating

9: pyridine / 0 deg C -> room temperature

With pyridine; triethylsilane; sodium azide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1080/15257779408013230

upstream raw materials:

benzoyl chloride

1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol

1,4-anhydro-D-ribitol

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol

Downstream raw materials:

1,4-anhydro-5-O-benzoyl-2-deoxy-2-<3,4-dihydro-4-oxo-1(2H)-pyrimidinyl>-D-lyxitol

5-O-benzoyl-2-deoxy-1,4-O²,3-anhydro-2-<3,4-dihydro-4-oxo-1(2H)-pyrimidinyl>-D-lyxitol