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

Base Information

• Chemical Name: 1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 500773-46-6
• Molecular Formula: C₃₁H₃₈N₂O₅Si
• Molecular Weight: 546.739
• Mol file: 500773-46-6.mol

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

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

There total 10 articles about 1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-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: 89.0%

Methylenetriphenylphosphorane (19493-09-5) + 3-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde (500773-45-5) → 1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (500773-46-6)

Guidance literature:

In tetrahydrofuran; at -78 - 0 ℃; for 2.5h;

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

Reference yield:

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) → 1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (500773-46-6)

Guidance literature:

Multi-step reaction with 9 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

6.1: imidazole / dimethylformamide / 12 h / 20 °C

7.1: 67 percent / aq. AcOH / tetrahydrofuran / 24 h / 20 °C

8.1: 98 percent / Dess-Martin periodinane; H₂O / CH₂Cl₂ / 1 h / 20 °C

9.1: 89 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; water; pyridinium trifluroacetate; sodium hydride; Dess-Martin periodane; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: Moffatt method / 9.1: Wittig reaction;

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

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (500773-46-6)

Guidance literature:

Multi-step reaction with 10 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

7.1: imidazole / dimethylformamide / 12 h / 20 °C

8.1: 67 percent / aq. AcOH / tetrahydrofuran / 24 h / 20 °C

9.1: 98 percent / Dess-Martin periodinane; H₂O / CH₂Cl₂ / 1 h / 20 °C

10.1: 89 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; water; pyridinium trifluroacetate; sodium hydride; Dess-Martin periodane; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Moffatt method / 10.1: Wittig reaction;

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

upstream raw materials:

Methylenetriphenylphosphorane

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

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