N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1-hydroxy-4-methylpent-4-en-1-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide

Base Information

Chemical Name:N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1-hydroxy-4-methylpent-4-en-1-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide
CAS No.:1616505-52-2
Molecular Formula:C₂₆H₂₈F₂N₂O₃S
Molecular Weight:486.583
Hs Code.:

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

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

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

There total 10 articles about N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1-hydroxy-4-methylpent-4-en-1-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][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: 23.0%

: 53750-52-0
4-iodo-2-methyl-but-1-ene

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

: 1616505-52-2
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1-hydroxy-4-methylpent-4-en-1-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide

Guidance literature:: 4-iodo-2-methyl-but-1-ene; With tert.-butyl lithium; In diethyl ether; at -78 ℃; for 0.583333h;

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-formyl-4,4-a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 1.41667h;

Reference yield:

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

: 1616505-52-2
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1-hydroxy-4-methylpent-4-en-1-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 8 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: tert.-butyl lithium / diethyl ether / 0.58 h / -78 °C

8.2: 1.42 h / -78 - 0 °C

With pyridine; sodium hypochlorite; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; tert.-butyl lithium; sulfur trioxide pyridine complex; boron trichloride; acetic acid; dimethyl sulfoxide; triethylamine; zinc; In diethyl ether; 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

: 1616505-52-2
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1-hydroxy-4-methylpent-4-en-1-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 7 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: tert.-butyl lithium / diethyl ether / 0.58 h / -78 °C

7.2: 1.42 h / -78 - 0 °C

With pyridine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; tert.-butyl lithium; sulfur trioxide pyridine complex; boron trichloride; acetic acid; dimethyl sulfoxide; triethylamine; zinc; In diethyl ether; n-heptane; dichloromethane; di-isopropyl ether; toluene;