Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester
• CAS No.: 145354-83-2
• Molecular Formula: C₁₆H₁₆N₂O₆
• Molecular Weight: 332.313
• Mol file: 145354-83-2.mol

Synonyms:Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

There total 11 articles about Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-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: 42.0%

5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-ol (149712-86-7) + (2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane (214273-21-9,145354-82-1) → Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester (145354-83-2) + Benzoic acid (2S,4R)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester (145354-84-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)60890-0

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester (145354-83-2)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / Ambient temperature

2: p-TsOH / methanol / Ambient temperature

3: NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / Ambient temperature

4: tetrahydrofuran / Ambient temperature

5: 44 percent / TMSOTf / 1,2-dichloro-ethane / 0 °C

With pyridine; sodium periodate; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; ruthenium(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60890-0

Reference yield:

Benzoic acid (2S,4S)-4-((R)-1,2-dihydroxy-ethyl)-[1,3]dioxolan-2-ylmethyl ester (145354-80-9) → Benzoic acid (2S,4S)-4-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester (145354-83-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / Ambient temperature

2: tetrahydrofuran / Ambient temperature

3: 44 percent / TMSOTf / 1,2-dichloro-ethane / 0 °C

With sodium periodate; trimethylsilyl trifluoromethanesulfonate; ruthenium(IV) oxide; In tetrahydrofuran; tetrachloromethane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60890-0

upstream raw materials:

5-Methyl-2-trimethylsilanyloxy-pyrimidin-4-ol

(2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane

benzoyl chloride

Benzoic acid (2S,4S)-4-((R)-1,2-dihydroxy-ethyl)-[1,3]dioxolan-2-ylmethyl ester

Downstream raw materials:

(+)-L-β-dioxolane-thymine