(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyridin-3-yl)-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-(5-fluoropyridin-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine
CAS No.:1621585-38-3
Molecular Formula:C₁₈H₁₆F₃N₃OS
Molecular Weight:379.406
Hs Code.:

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

There total 14 articles about (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyridin-3-yl)-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:

: 946002-10-4
(5-fluoropyridin-2-yl)boronic acid

: 1621585-55-4
(4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

: 1621585-38-3
(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyridin-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: (5-fluoropyridin-2-yl)boronic acid; (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate; With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; water; at 65 ℃; for 17h;

With 20% palladium hydroxide-activated charcoal; hydrogen; trifluoroacetic acid; In methanol; at 50 ℃; for 16h; under 2585.81 Torr;

With methylamine; In ethanol; at 65 ℃; for 16h;

Reference yield:

: 1220328-94-8
({[(2R)-2-(2,2-diethoxyethoxy)pent-4-en-1-yl]oxy}methyl)benzene

: 1621585-38-3
(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyridin-3-yl)-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: formic acid / water / 2.5 h / 20 °C

1.2: 18 h / 20 °C

2.1: sodium hypochlorite / water; dichloromethane / 1.5 h / 0 - 15 °C

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

3.2: 1.5 h / -76 - -71 °C

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

5.1: dichloromethane / 18 h / 20 °C

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

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

8.1: triethylamine / dichloromethane / 0.08 h / 20 °C

8.2: 6.5 h / 20 °C

9.1: potassium carbonate / acetonitrile / 20.5 h / 20 °C / Inert atmosphere; Reflux

10.1: ruthenium trichloride; sodium periodate / water; acetonitrile; 1,2-dichloro-ethane / 21 h / 20 °C

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

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

12.2: 16 h / 50 °C / 2585.81 Torr

12.3: 16 h / 65 °C

With pyridine; ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium hypochlorite; sodium periodate; formic acid; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; boron trichloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; n-heptane; dichloromethane; di-isopropyl ether; water; 1,2-dichloro-ethane; toluene; acetonitrile;

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

: 1621585-38-3
(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyridin-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: triethylamine / dichloromethane / 0.08 h / 20 °C

2.2: 6.5 h / 20 °C

3.1: potassium carbonate / acetonitrile / 20.5 h / 20 °C / Inert atmosphere; Reflux

4.1: ruthenium trichloride; sodium periodate / water; acetonitrile; 1,2-dichloro-ethane / 21 h / 20 °C

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

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

6.2: 16 h / 50 °C / 2585.81 Torr

6.3: 16 h / 65 °C

With ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; boron trichloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; triethylamine; In tetrahydrofuran; n-heptane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;