(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Base Information

Chemical Name:(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine
CAS No.:1622327-94-9
Molecular Formula:C₁₉H₁₇F₃N₂OS
Molecular Weight:378.418
Hs Code.:

Synonyms:(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

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Chemical Property of (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

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Technology Process of (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

There total 17 articles about (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[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:

: C₂₆H₂₁F₃N₂O₂S

: 1622327-94-9
(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 65 ℃; for 16h;

Reference yield:

: N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-20 4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

: 1622327-94-9
(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: Multi-step reaction with 8 steps

1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C

2: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 6.5 h / 20 °C

3: potassium carbonate / acetonitrile / 2.5 h / Reflux; Inert atmosphere

4: sodium periodate; ruthenium trichloride / water; acetonitrile; 1,2-dichloro-ethane / 3 h / 20 °C

5: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

6: caesium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 17 h / 65 °C

7: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 2 h / 20 °C / Cooling

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

With methanol; triethylsilane; ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; sulfur trioxide pyridine complex; boron trichloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; n-heptane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; 6: |Suzuki Coupling;

Reference yield:

: 1220328-97-1
(3aR,5R)-5-[(benzyloxy)methyl]-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole

: 1622327-94-9
(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(4-fluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: Multi-step reaction with 12 steps

1.1: boron trifluoride diethyl etherate / toluene; di-isopropyl ether / 0.5 h / -76 °C

1.2: -76 - -71 °C

2.1: acetic acid; zinc / 20 - 40 °C

3.1: dichloromethane / 18 h / 20 °C

4.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 3 h / -60 - -5 °C

5.1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C

6.1: tetrapropylammonium permanganate; 4-methylmorpholine N-oxide / acetonitrile / 1.5 h / 20 °C

7.1: tetrahydrofuran; acetic acid / 18 h / 20 °C

8.1: trifluoroacetic acid; pyridinium chlorochromate / acetonitrile / 3.5 h / 20 °C

9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

10.1: caesium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 17 h / 65 °C

11.1: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 2 h / 20 °C / Cooling

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 16 h / 65 °C

With pyridine; methanol; triethylsilane; bis-triphenylphosphine-palladium(II) chloride; tetrapropylammonium permanganate; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; boron trichloride; potassium hexamethylsilazane; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; trifluoroacetic acid; zinc; In tetrahydrofuran; n-heptane; dichloromethane; di-isopropyl ether; water; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile; 10.1: |Suzuki Coupling;