3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 192564-27-5
• Molecular Formula: C₅₅H₅₇N₂O₆PSi
• Molecular Weight: 901.127

Synonyms:

Chemical Property of 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-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 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

There total 10 articles about 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-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: 43.0%

triphenylphosphine (603-35-0) + 3-Benzyloxymethyl-1-[(2R,4S,5R)-5-(4-bromo-3-oxo-butyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (192564-25-3) → 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (192564-27-5)

Guidance literature:

With sodium hydrogencarbonate; In benzene; for 16h; Ambient temperature;

DOI:10.1016/S0960-894X(97)00269-2

Reference yield:

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (192564-27-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / CH₂Cl₂ / 1.5 h / 0 °C

2: 94 percent / H₂ / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

3: 100 percent / DBU / acetonitrile / 24 h / 0 - 20 °C

4: 92 percent / LiOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

5: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C to 0 deg C, 1.5 h, 2.) THF, -78 deg C to room temp., 5 h

With lithium hydroxide; hydrogen; pivaloyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0960-894X(97)00269-2

Reference yield:

(E)-3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acrylic acid methyl ester → 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (192564-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / H₂ / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

2: 100 percent / DBU / acetonitrile / 24 h / 0 - 20 °C

3: 92 percent / LiOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C to 0 deg C, 1.5 h, 2.) THF, -78 deg C to room temp., 5 h

With lithium hydroxide; hydrogen; pivaloyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1016/S0960-894X(97)00269-2

upstream raw materials:

triphenylphosphine

3-Benzyloxymethyl-1-[(2R,4S,5R)-5-(4-bromo-3-oxo-butyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Methylenetriphenylphosphorane

3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid

Downstream raw materials:

C₆₃H₈₁N₇O₁₀Si₂

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