(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

Base Information

• Chemical Name: (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
• CAS No.: 1262803-52-0
• Molecular Formula: C₁₃H₁₃F₂N₃O₄
• Molecular Weight: 313.261

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 11 articles about (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 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:

(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-ylamine (1262803-51-9) → (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)

Guidance literature:

(4aR,5S,7aS)-5-fluoromethyl-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-ylamine; With sulfuric acid; nitric acid; trifluoroacetic acid; at 0 ℃; for 0.75h;

With sodium hydroxide; In water; pH=12;

Reference yield:

1-benzoyl-3-[(3S,4R,5S)-3-(2-fluorophenyl)-4-hydroxymethyl-5-trityloxymethyl-tetrahydrofuran-3-yl]thiourea (1174321-96-0) → (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)

Guidance literature:

Multi-step reaction with 5 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

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;

Reference yield:

ethyl ((S)-1-trityloxymethylallyloxy)acetate (1174321-91-5) → (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)

Guidance literature:

Multi-step reaction with 11 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

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:

ethyl ((S)-1-trityloxymethylallyloxy)acetate

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

[(2S,3R,4S)-4-amino-4-(2-fluorophenyl)-2-trityloxymethyl-tetrahydrofuran-3-yl]methanol

1-benzoyl-3-[(3S,4R,5S)-3-(2-fluorophenyl)-4-hydroxymethyl-5-trityloxymethyl-tetrahydrofuran-3-yl]thiourea

Downstream raw materials:

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

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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