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

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 2-trimethylsilanyl-ethyl ester
• CAS No.: 174358-67-9
• Molecular Formula: C₄₉H₅₇N₃O₁₅Si
• Molecular Weight: 956.088
• Mol file: 174358-67-9.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 2-trimethylsilanyl-ethyl ester

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 2-trimethylsilanyl-ethyl ester

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 2-trimethylsilanyl-ethyl ester

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 2-trimethylsilanyl-ethyl 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:

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) + C18H26ClNO8Si → 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)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 25 ℃; for 2h; Yield given;

DOI:10.1021/jo951550w

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → 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 2-trimethylsilanyl-ethyl ester (174358-67-9)

Guidance literature:

Multi-step reaction with 4 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

With sodium tetrahydroborate; nitric acid; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol;

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 2-trimethylsilanyl-ethyl ester (174358-67-9)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jo951550w

upstream raw materials:

5'-O-(4-4'-dimethoxytrityl)thymidine

2-(Trimethylsilyl)ethanol

vanillin

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

Downstream 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