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

Base Information

• Chemical Name: N-[(4aR,6R,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide
• CAS No.: 1669434-23-4
• Molecular Formula: C₂₇H₂₁F₂N₃O₂S
• Molecular Weight: 489.545
• Mol file: 1669434-23-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about N-[(4aR,6R,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide 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: 58.0%

N-[(4aR,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669433-79-7) → N-[(4aR,6R,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669434-23-4)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In 1,2-dichloro-ethane; at 0 - 20 ℃; 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 → N-[(4aR,6R,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669434-23-4)

Guidance literature:

Multi-step reaction with 7 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 / 16 h / 0 - 20 °C

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

Reference yield:

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4-a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide → N-[(4aR,6R,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669434-23-4)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

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

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

6: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 16 h / 0 - 20 °C

With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; tetrapropylammonium permanganate; potassium hexamethylsilazane; caesium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; water; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile; 5: |Suzuki Coupling;

upstream raw materials:

N-[(4aR,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}acetaldehyde

2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine

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

Downstream raw materials:

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