1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 500773-48-8
• Molecular Formula: C₃₅H₃₈N₂O₈
• Molecular Weight: 614.695
• Mol file: 500773-48-8.mol

Synonyms:

Chemical Property of 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

There total 6 articles about 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 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: 64.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-((2R,4S)-4-Allyloxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (500773-43-3) → 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (500773-48-8)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(02)01926-3

Reference yield:

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) → 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (500773-48-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / NaH in oil / tetrahydrofuran / 4 h / 40 °C / ultrasound irradiation

2.1: 96 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: DCC; pyridinium trifluoroacetate / dimethylsulfoxide / 12 h / 20 °C

4.1: aq NaOH / dioxane / 6 h / 20 °C

4.2: NaBH₄ / dioxane / 0.5 h / 20 °C

5.1: 64 percent / pyridine / 3 h / 20 °C

With pyridine; sodium hydroxide; tetrabutyl ammonium fluoride; pyridinium trifluroacetate; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dimethyl sulfoxide; 3.1: Moffatt method;

DOI:10.1016/S0040-4039(02)01926-3

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-{(2R,4S,5S)-4-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (500773-48-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 87 percent / imidazole / dimethylformamide / 6 h / 20 °C

2.1: 80 percent / NaH in oil / tetrahydrofuran / 4 h / 40 °C / ultrasound irradiation

3.1: 96 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: DCC; pyridinium trifluoroacetate / dimethylsulfoxide / 12 h / 20 °C

5.1: aq NaOH / dioxane / 6 h / 20 °C

5.2: NaBH₄ / dioxane / 0.5 h / 20 °C

6.1: 64 percent / pyridine / 3 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; pyridinium trifluroacetate; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Moffatt method;

DOI:10.1016/S0040-4039(02)01926-3

upstream raw materials:

4,4'-dimethoxytrityl chloride

1-((2R,4S)-4-Allyloxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

thymidine

Downstream raw materials:

1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

3-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-[4-allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione