(2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester
• CAS No.: 339178-22-2
• Molecular Formula: C₂₀H₂₃FN₂O₈S
• Molecular Weight: 470.476
• Mol file: 339178-22-2.mol

Synonyms:(2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Chemical Property of (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

There total 8 articles about (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester 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: 48.0%

N-fluorobis(benzenesulfon)imide (133745-75-2) + (2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-10-8) → 3-benzenesulfonyloxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester + (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-22-2)

Guidance literature:

(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; cyclohexane; at -78 - 20 ℃;

With tert.-butyl lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane; at -78 ℃; for 1h;

N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 25 ℃; Further stages.;

DOI:10.1021/jo001223a

Reference yield: 21.0%

N-fluorobis(benzenesulfon)imide (133745-75-2) + (2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-10-8) → (2S,3S,5R)-2-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester + (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-22-2)

Guidance literature:

(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; cyclohexane; at -78 - 20 ℃;

With tert.-butyl lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane; at -78 ℃; for 1h;

N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 78 ℃; for 0.166667h; Further stages.;

DOI:10.1021/jo001223a

Reference yield:

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid (127244-82-0) → (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-22-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 23.5 h / 0 - 20 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

3.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / -78 - 20 °C

3.2: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

3.3: 19 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / 78 °C

With dmap; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; cyclohexane;

DOI:10.1021/jo001223a

upstream raw materials:

N-fluorobis(benzenesulfon)imide

(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester