4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid

Base Information

• Chemical Name: 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid
• CAS No.: 174358-72-6
• Molecular Formula: C₄₄H₄₅N₃O₁₅
• Molecular Weight: 855.852
• Mol file: 174358-72-6.mol

Synonyms:4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid

Chemical Property of 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid

There total 7 articles about 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid 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: 59.0%

4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid 2-trimethylsilanyl-ethyl ester (174358-67-9) → 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid (174358-72-6)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 35 ℃; for 36h;

DOI:10.1021/jo951550w

Reference yield:

vanillin (121-33-5,8014-42-4) → 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid (174358-72-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / K₂CO₃, n-Bu₄NI / acetonitrile / 2 h / Heating

2: 99 percent / LiOH / dioxane / 8 h / Ambient temperature

3: 1.) fuming HNO₃, AcOH, 2.) DCC / 1.) 6 h, 2.) EtOAc, CH₂Cl₂, 5 h, room temperature

4: 72 percent / NaBH₄ / ethanol / 3 h / Ambient temperature

5: tetrahydrofuran / 4 h

6: NaH / tetrahydrofuran / 2 h / 25 °C

7: 59 percent / CsF / dimethylformamide / 36 h / 35 °C

With lithium hydroxide; sodium tetrahydroborate; nitric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; dicyclohexyl-carbodiimide; cesium fluoride; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo951550w

Reference yield:

4-(4-formyl-2-methoxyphenoxy)butyric acid (174358-69-1) → 4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid (174358-72-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) fuming HNO₃, AcOH, 2.) DCC / 1.) 6 h, 2.) EtOAc, CH₂Cl₂, 5 h, room temperature

2: 72 percent / NaBH₄ / ethanol / 3 h / Ambient temperature

3: tetrahydrofuran / 4 h

4: NaH / tetrahydrofuran / 2 h / 25 °C

5: 59 percent / CsF / dimethylformamide / 36 h / 35 °C

With sodium tetrahydroborate; nitric acid; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; cesium fluoride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo951550w

upstream raw materials:

4-{4-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxymethyl]-2-methoxy-5-nitro-phenoxy}-butyric acid 2-trimethylsilanyl-ethyl ester

vanillin

4-(4-formyl-2-methoxyphenoxy)butyric acid

4-(4-formyl-2-methoxyphenoxy)butanoic acid methyl ester