(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

Base Information

Chemical Name:(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole
CAS No.:1613393-58-0
Molecular Formula:C₂₀H₂₀BrF₂NO₃
Molecular Weight:440.285
Hs Code.:

Synonyms:(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

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Chemical Property of (3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

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Technology Process of (3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

There total 5 articles about (3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole 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: 74.0%

: 28342-75-8
1,5-dibromo-2,4-difluorobenzene

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

: 1613393-58-0
(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

Guidance literature:: 1,5-dibromo-2,4-difluorobenzene; (3aR,5R)-5-[(benzyloxy)methyl]-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole; With boron trifluoride diethyl etherate; In toluene; at -78 ℃; for 0.5h; Inert atmosphere;

With n-butyllithium; In hexane; toluene; at -78 - 5 ℃; for 1.5h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.6b01451

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 1613393-58-0
(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 30 °C

1.2: 19 h / 20 - 70 °C

2.1: formic acid; water / 2.5 h / 20 °C

2.2: 18 h / 20 °C

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

4.1: boron trifluoride diethyl etherate / toluene; isopropyl alcohol / 0.5 h / -74 °C / Inert atmosphere

4.2: 1.5 h / -78 - 5 °C

With sodium hypochlorite; formic acid; boron trifluoride diethyl etherate; water; sodium hydride; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; toluene; mineral oil;

Reference yield:

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

: 1613393-58-0
(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

Guidance literature:: Multi-step reaction with 3 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; isopropyl alcohol / 0.5 h / -74 °C / Inert atmosphere

3.2: 1.5 h / -78 - 5 °C

With sodium hypochlorite; formic acid; boron trifluoride diethyl etherate; water; In dichloromethane; water; isopropyl alcohol; toluene;