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

Base Information

Chemical Name: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
CAS No.:1315584-51-0
Molecular Formula:C₂₄H₃₃FN₂O₇Si
Molecular Weight:508.619
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 100.0%

: 1160557-97-0
1-((2R,3R,4R,5R)-5-((tert-butyldimethylsilyloxy)methyl)-3-fluoro-4-hydroxy-3-methyl-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

: 501-53-1,94274-21-2
benzyl chloroformate

: 1315584-51-0
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

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃;

Reference yield: 75.0%

: 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide

: 1160557-97-0
1-((2R,3R,4R,5R)-5-((tert-butyldimethylsilyloxy)methyl)-3-fluoro-4-hydroxy-3-methyl-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

: 1315584-51-0
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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1002/ejoc.201800158

Reference yield:

: 863329-66-2,2041584-99-8
2'-deoxy-2'-fluoro-2'-methyluridine

: 1315584-51-0
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

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole; pyridine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201800158