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

Base Information

• Chemical Name: (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine
• CAS No.: 1391001-94-7
• Molecular Formula: C₁₃H₁₃F₂N₃O₃S
• Molecular Weight: 329.327
• Mol file: 1391001-94-7.mol

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

Chemical Property of (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

There total 8 articles about (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-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:

N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (1174322-00-9) → (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (1391001-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 5 h / Reflux

2.1: nitric acid; trifluoroacetic acid; sulfuric acid / 0.92 h / 0 °C

2.2: pH 12

With methanol; sulfuric acid; nitric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid;

Reference yield:

N-(((3S,4R,5S)-5-(fluoromethyl)-3-(2-fluorophenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide (1391001-93-6) → (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (1391001-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 0 - 18 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 5 h / Reflux

3.1: nitric acid; trifluoroacetic acid; sulfuric acid / 0.92 h / 0 °C

3.2: pH 12

With pyridine; methanol; trifluoromethylsulfonic anhydride; sulfuric acid; nitric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane;

Reference yield:

tert-butyl (S)-2-((1-fluorobut-3-en-2-yl)oxy)acetate (1391001-87-8) → (4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (1391001-94-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: formic acid / 0 - 20 °C

2.1: 1,1'-carbonyldiimidazole / dichloromethane / 3 - 20 °C

2.2: 3 - 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -60 °C / Inert atmosphere

3.2: -78 - -60 °C

4.1: hydroxylamine hydrochloride; sodium acetate / methanol / 1.5 h / 50 °C

5.1: hydroquinone / xylene / 5 h / Reflux

6.1: zinc; acetic acid / 0 - 20 °C

7.1: dichloromethane / 18 h / 0 - 20 °C

8.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 0 - 18 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 5 h / Reflux

10.1: nitric acid; trifluoroacetic acid; sulfuric acid / 0.92 h / 0 °C

10.2: pH 12

With pyridine; methanol; n-butyllithium; formic acid; trifluoromethylsulfonic anhydride; sulfuric acid; hydroxylamine hydrochloride; nitric acid; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydroquinone; 1,1'-carbonyldiimidazole; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; xylene;

upstream raw materials:

N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

tert-butyl (S)-2-((1-fluorobut-3-en-2-yl)oxy)acetate

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-N-methoxy-N-methylacetamide

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-1-(2-fluorophenyl)ethanone

Downstream raw materials:

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

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

tert-butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-(5-methoxypyrazine-2-carboxamido)phenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate