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

Base Information

Chemical Name:(4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine
CAS No.:1616504-52-9
Molecular Formula:C₁₆H₁₈F₂N₂OS
Molecular Weight:324.395
Hs Code.:

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

There total 11 articles about (4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-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: 40.0%

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

: 1616504-52-9
(4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

: 1616504-98-3
(±)-(4aS,6S,8aR)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 80 ℃; for 9h;

Reference yield:

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

: 1616504-52-9
(4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-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 trifluoride diethyl etherate / toluene / 0.5 h / -76 - -73 °C / Inert atmosphere

1.2: 1.25 h / -75 - -73 °C / Inert atmosphere

2.1: acetic acid; zinc / 18 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 15 h / 20 °C / Inert atmosphere

4.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 1.5 h / -50 - 0 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 9 h / 80 °C / Inert atmosphere

6.1: isopropylamine; carbon dioxide / methanol / Resolution of racemate

With pyridine; trifluoromethylsulfonic anhydride; carbon dioxide; boron trifluoride diethyl etherate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; isopropylamine; zinc; In methanol; dichloromethane; toluene;
DOI:10.1021/jm501833t

Reference yield:

: (±)-(3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

: 1616504-52-9
(4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Guidance literature:: Multi-step reaction with 5 steps

1: acetic acid; zinc / 18 h / 20 °C / Inert atmosphere

2: dichloromethane / 15 h / 20 °C / Inert atmosphere

3: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 1.5 h / -50 - 0 °C / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 9 h / 80 °C / Inert atmosphere

5: isopropylamine; carbon dioxide / methanol / Resolution of racemate

With pyridine; trifluoromethylsulfonic anhydride; carbon dioxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; isopropylamine; zinc; In methanol; dichloromethane;
DOI:10.1021/jm501833t