benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate

Base Information

• Chemical Name: benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate
• CAS No.: 1256490-58-0
• Molecular Formula: C₁₈H₁₉FN₂O₇
• Molecular Weight: 394.356
• Mol file: 1256490-58-0.mol

Synonyms:benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate

Chemical Property of benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate

There total 4 articles about benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate 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: 98.0%

benzyl (2R,3R,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-3-yl carbonate (1315584-51-0) → benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate (1256490-58-0)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.046

Reference yield:

2'-deoxy-2'-fluoro-2'-methyluridine (863329-66-2,2041584-99-8) → benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate (1256490-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; 1H-imidazole / 0 - 20 °C / Inert atmosphere

2: dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

3: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.05.046

Reference yield:

1-((2R,3R,4R,5R)-5-((tert-butyldimethylsilyloxy)methyl)-3-fluoro-4-hydroxy-3-methyl-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (1160557-97-0) → benzyl (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl carbonate (1256490-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

2: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With dmap; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.05.046

upstream raw materials:

2'-deoxy-2'-fluoro-2'-methyluridine

1-((2R,3R,4R,5R)-5-((tert-butyldimethylsilyloxy)methyl)-3-fluoro-4-hydroxy-3-methyl-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

benzyl (2R,3R,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-3-yl carbonate

benzyl chloroformate

Downstream raw materials:

(S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid ethyl ester

C₂₉H₃₃FN₃O₁₁P