(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-amine trifluoroacetate

Base Information

Chemical Name:(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-amine trifluoroacetate
CAS No.:1616504-51-8
Molecular Formula:C₂HF₃O₂*C₁₇H₂₀F₂N₂O₂S
Molecular Weight:468.445
Hs Code.:

Synonyms:(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-amine trifluoroacetate

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Chemical Property of (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-amine trifluoroacetate

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Technology Process of (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-amine trifluoroacetate

There total 13 articles about (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-amine trifluoroacetate 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: 82.0%

: 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

: 76-05-1
trifluoroacetic acid

: 1616504-51-8
(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-amine trifluoroacetate

Guidance literature:: 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; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 80 ℃; for 7h; Sealed tube;

trifluoroacetic acid; In acetonitrile;

Reference yield:

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

: 1616504-51-8
(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-amine trifluoroacetate

Guidance literature:: Multi-step reaction with 11 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

11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 7 h / 80 °C / Sealed tube

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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; In tetrahydrofuran; methanol; 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

: 1616504-51-8
(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-amine trifluoroacetate

Guidance literature:: Multi-step reaction with 10 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

10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 7 h / 80 °C / Sealed tube

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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; In tetrahydrofuran; methanol; n-heptane; dichloromethane; di-isopropyl ether; toluene;