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

Base Information

Chemical Name:N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(tetrahydrofuran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide
CAS No.:1616504-86-9
Molecular Formula:C₂₄H₂₄F₂N₂O₃S
Molecular Weight:458.529
Hs Code.:

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

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

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

There total 12 articles about N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(tetrahydrofuran-2-yl)-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: 84.0%

: 1616504-84-7
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1,4-dihydroxybutyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

: 1616504-86-9
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(tetrahydrofuran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 0 ℃; for 0.5h;

Reference yield:

: 1220328-95-9
2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine

: 1616504-86-9
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(tetrahydrofuran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hypochlorite / water; dichloromethane / 0 - 15 °C

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

2.2: 1.5 h / -76 - -71 °C

3.1: acetic acid; zinc / 16 h / 20 - 40 °C

4.1: dichloromethane / 18 h / 20 °C

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

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

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

8.1: magnesium; iodine / tetrahydrofuran / 1.42 h / 26 - 40 °C

8.2: 2 h / -78 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

10.1: trifluoromethylsulfonic anhydride; 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; sodium hypochlorite; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; sulfur trioxide pyridine complex; boron trichloride; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; n-heptane; dichloromethane; di-isopropyl ether; water; toluene;

Reference yield:

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

: 1616504-86-9
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(tetrahydrofuran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: 1.5 h / -76 - -71 °C

2.1: acetic acid; zinc / 16 h / 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: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 6.5 h / 20 °C

7.1: magnesium; iodine / tetrahydrofuran / 1.42 h / 26 - 40 °C

7.2: 2 h / -78 - 20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

9.1: trifluoromethylsulfonic anhydride; 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; sulfur trioxide pyridine complex; boron trichloride; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; n-heptane; dichloromethane; di-isopropyl ether; toluene;