(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione
• CAS No.: 865838-15-9
• Molecular Formula: C₃₉H₃₂F₂N₂O₆
• Molecular Weight: 662.69
• Mol file: 865838-15-9.mol

Synonyms:(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione

Chemical Property of (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione

There total 3 articles about (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-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: 78.0%

→ (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione (865838-15-9)

Guidance literature:

Reference yield:

3-benzoyl-5-fluorouracil (61251-77-2) + (3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-42-5) → (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione (865838-15-9)

Guidance literature:

3-benzoyl-5-fluorouracil; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

(3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.ejmech.2018.06.003

Reference yield:

tert-butyl(((3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane (805245-41-4) → (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-5-fluoro-1H-pyrimidine-2,4-dione (865838-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 20 °C

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/j.ejmech.2018.06.003

upstream raw materials:

3-benzoyl-5-fluorouracil

(3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

tert-butyl(((3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane