tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate
• CAS No.: 1262803-53-1
• Molecular Formula: C₁₈H₂₁F₂N₃O₆
• Molecular Weight: 413.378

Synonyms:tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate

Chemical Property of tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate

There total 12 articles about tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate 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:

di-tert-butyl dicarbonate (24424-99-5) + (4aR,5S,7aS)-5-(fluoromethyl)-7a-(2-fluoro-5-nitrophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-amine (1262803-52-0) → tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate (1262803-53-1)

Guidance literature:

With triethylamine; In dichloromethane; for 20h;

Reference yield:

1-benzoyl-3-[(3S,4R,5S)-3-(2-fluorophenyl)-4-hydroxymethyl-5-trityloxymethyl-tetrahydrofuran-3-yl]thiourea (1174321-96-0) → tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate (1262803-53-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dicyclohexyl-carbodiimide / ethanol / 6 h / 80 °C

2.1: formic acid / 20 °C

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

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 16 h / 65 °C

5.1: nitric acid; trifluoroacetic acid; sulfuric acid / 0.75 h / 0 °C

5.2: pH 12

6.1: triethylamine / dichloromethane / 20 h

With formic acid; Nonafluorobutanesulfonyl fluoride; sulfuric acid; nitric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane;

Reference yield:

ethyl ((S)-1-trityloxymethylallyloxy)acetate (1174321-91-5) → tert-butyl [(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluoro-5-nitrophenyl)-4a,5,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate (1262803-53-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: hydroxylamine hydrochloride; sodium acetate / methanol / 0.25 h / 20 °C

3.1: sodium hypochlorite / dichloromethane / 0.5 h / 0 °C

4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

4.2: 0.67 h / -78 °C

5.1: zinc; acetic acid / 18 h / 20 °C

6.1: dichloromethane / 0.17 h / 20 °C

7.1: dicyclohexyl-carbodiimide / ethanol / 6 h / 80 °C

8.1: formic acid / 20 °C

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

10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 16 h / 65 °C

11.1: nitric acid; trifluoroacetic acid; sulfuric acid / 0.75 h / 0 °C

11.2: pH 12

12.1: triethylamine / dichloromethane / 20 h

With sodium hypochlorite; n-butyllithium; formic acid; Nonafluorobutanesulfonyl fluoride; sulfuric acid; hydroxylamine hydrochloride; nitric acid; sodium acetate; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene;

upstream raw materials:

di-tert-butyl dicarbonate

(4aR,5S,7aS)-5-(fluoromethyl)-7a-(2-fluoro-5-nitrophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-amine

ethyl ((S)-1-trityloxymethylallyloxy)acetate

(3aR,4S)-4-((trityloxy)methyl)-3,3a,4,6-tetrahydrofuro[3,4-c]isoxazole

Downstream raw materials:

N-(3-((4aR,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-7a-yl)-4-fluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide

tert-butyl [(4aR,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-fluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-yl]carbamate

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