1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione
• CAS No.: 150109-60-7
• Molecular Formula: C₂₂H₃₀F₂N₂O₅Si
• Molecular Weight: 468.573
• Mol file: 150109-60-7.mol

Synonyms:

Chemical Property of 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione

There total 3 articles about 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-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:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione (150109-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / imidazole / dimethylformamide / 5.5 h / -30 °C

2: 1.) aq. KOH / 1.) toluene, dioxane, RT, 2.5 h, 2.) toluene, dioxane, RT, 6 h

With 1H-imidazole; potassium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.44.1196

Reference yield:

5-Fluoro-2'-deoxyuridine (50-91-9) → 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione (150109-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / imidazole / dimethylformamide / 5.5 h / -30 °C

2: 1.) aq. KOH / 1.) toluene, dioxane, RT, 2.5 h, 2.) toluene, dioxane, RT, 6 h

With 1H-imidazole; potassium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.44.1196

Reference yield:

5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-fluorouridine (129816-30-4) + 4-Fluorobenzyl bromide (459-46-1) → 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione (150109-60-7)

Guidance literature:

With potassium hydroxide; Multistep reaction; 1.) toluene, dioxane, RT, 2.5 h, 2.) toluene, dioxane, RT, 6 h;

DOI:10.1248/cpb.44.1196

upstream raw materials:

5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-fluorouridine

4-Fluorobenzyl bromide

tert-butyldimethylsilyl chloride

5-Fluoro-2'-deoxyuridine

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester