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

Base Information

• Chemical Name: (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate
• CAS No.: 1621585-55-4
• Molecular Formula: C₂₁H₁₅F₅N₂O₅S₂
• Molecular Weight: 534.485
• Mol file: 1621585-55-4.mol

Synonyms:(4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

Chemical Property of (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

There total 11 articles about (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate 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: 73.0%

N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-oxo-4,4-a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide + N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) → (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate (1621585-55-4)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1.43h;

Reference yield:

[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (1425947-62-1) → (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate (1621585-55-4)

Guidance literature:

Multi-step reaction with 7 steps

1: dichloromethane / 18 h / 20 °C

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

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

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

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

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

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

With pyridine; tetrapropylammonium permanganate; trifluoromethylsulfonic anhydride; boron trichloride; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; n-heptane; dichloromethane; acetic acid; toluene; acetonitrile;

Reference yield:

N-{[(3S,4R,6R)-6-[(benzyloxy)methyl]-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide → (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate (1621585-55-4)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

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

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

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

With pyridine; tetrapropylammonium permanganate; trifluoromethylsulfonic anhydride; boron trichloride; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; n-heptane; dichloromethane; acetic acid; toluene; acetonitrile;

upstream raw materials:

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

[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol

(4aR,6S,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-6-yl acetate

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

Downstream 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

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

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

(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