(2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Base Information

• Chemical Name: (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole
• CAS No.: 636603-74-2
• Molecular Formula: C₂₀H₂₇NO₂
• Molecular Weight: 313.44

Synonyms:(2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Chemical Property of (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Chemical Property:

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• Pictogram(s):  
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Technology Process of (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

There total 3 articles about (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole 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: 90.0%

(2S,3S,3aS,4aS,5R,8S,8aR)-3-nitro-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole (636603-69-5) → (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole (636603-74-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Heating;

DOI:10.1055/s-2003-40191

Reference yield:

(+)-3-(hydroxylamino)isoborneol hydrochloride → (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole (636603-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1: CaCO₃ / CH₂Cl₂ / 4 h / 45 °C

2: CH₂Cl₂ / 18 h / Heating

3: 90 percent / Bu₃SnH; AIBN / benzene / 2 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; calcium carbonate; In dichloromethane; benzene;

DOI:10.1055/s-2003-40191

Reference yield:

(1R,2S,6R,7S)-1,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene 5-oxide (171020-83-0) → (2S,3S,3aS,4aS,5R,8S,8aR)-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole (636603-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 18 h / Heating

2: 90 percent / Bu₃SnH; AIBN / benzene / 2 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; benzene;

DOI:10.1055/s-2003-40191

upstream raw materials:

(2S,3S,3aS,4aS,5R,8S,8aR)-3-nitro-2-phenyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

(1R,2S,6R,7S)-1,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide

Downstream raw materials:

(2S,3R)-methyl 3-hydroxy-2-methyl-3-phenylpropionate

(+)-(2S,3R)-3-hydroxy-2-methyl-3-phenylpropanoic acid

(2S,3R)-3-Hydroxy-2-methyl-3-phenyl-propionaldehyde

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