1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione
• CAS No.: 321684-76-8
• Molecular Formula: C₃₀H₅₀N₂O₆Si₂
• Molecular Weight: 590.908
• Mol file: 321684-76-8.mol

Synonyms:1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione

Chemical Property of 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione

There total 1 articles about 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-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: 75.0%

hydrocinnamic acid chloride (645-45-4) + 2′-deoxy-3′,5′-bis-O-[(tert-butyl)dimethylsilyl]-5,6-dihydrouridine (187980-02-5) → 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione (321684-76-8)

Guidance literature:

With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃;

DOI:10.1021/jo0007433

Reference yield: 91.0%

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione (321684-76-8) → 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-1H-pyrimidine-2,4-dione (321684-78-0)

Guidance literature:

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione; With pyridine; Phenylselenyl chloride; In dichloromethane; at 0 - 20 ℃;

With dihydrogen peroxide; In dichloromethane; water; at 0 - 20 ℃; Further stages.;

DOI:10.1021/jo0007433

Reference yield:

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-dihydro-pyrimidine-2,4-dione (321684-76-8) → methanesulfonic acid 1-{1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-3-phenyl-propyl ester

Guidance literature:

Multi-step reaction with 3 steps

1.1: phenylselenyl chloride; pyridine / CH₂Cl₂ / 0 - 20 °C

1.2: 91 percent / H₂O₂ / H₂O; CH₂Cl₂ / 0 - 20 °C

2.1: 58 percent / NaBH₄; CeCl₃-7H₂O / methanol / 0.25 h

3.1: triethylamine / CH₂Cl₂ / 2.5 h / 0 °C

With pyridine; sodium tetrahydroborate; Phenylselenyl chloride; cerium(III) chloride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo0007433

upstream raw materials:

hydrocinnamic acid chloride

2′-deoxy-3′,5′-bis-O-[(tert-butyl)dimethylsilyl]-5,6-dihydrouridine

Downstream raw materials:

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(3-phenyl-propionyl)-1H-pyrimidine-2,4-dione

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(1-hydroxy-3-phenyl-propyl)-1H-pyrimidine-2,4-dione

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-[1-(2-hydroxy-ethylsulfanyl)-3-phenyl-propyl]-1H-pyrimidine-2,4-dione