(4aR,8aS,R_S)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran

Base Information

• Chemical Name: (4aR,8aS,R_S)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran
• CAS No.: 148587-66-0
• Molecular Formula: C₂₁H₃₀O₂S
• Molecular Weight: 346.534

Synonyms:(4aR,8aS,R_S)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran

Chemical Property of (4aR,8aS,R_S)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran

Chemical Property:

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Technology Process of (4aR,8aS,R_S)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran

There total 1 articles about (4aR,8aS,R_S)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran 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:

(R)-(+)-(E)-1-(p-toluenesulfinyl)-6,6,10-trimethyl-3,9-undecadien-2-one (148587-65-9) → (4aS,8aR,RS)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran (148587-67-1) + (4aR,8aS,RS)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran (148587-66-0)

Guidance literature:

With diethylaluminium chloride; In toluene; at -78 ℃; for 1h; Product distribution; other Lewis acids; other solvent; var. temp.;

DOI:10.1248/cpb.45.759

Reference yield: 86.0%

(4aR,8aS,RS)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran (148587-66-0) → (4aR,8aS)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfenylmethyl)-1H-2-benzopyran

Guidance literature:

With titanium(III) chloride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1248/cpb.45.759

Reference yield:

(4aR,8aS,RS)-4a,5,6,7,8,8a-hexahydro-1,1,6,6-tetramethyl-2-(p-toluenesulfinylmethyl)-1H-2-benzopyran (148587-66-0) → (4aS,8aS)-(-)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-(p-toluenesulfenyl)-1H-2-benzopyran (145627-38-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / Na, iPrOH / tetrahydrofuran / 2 h / Ambient temperature

2: 35 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 2 h / Ambient temperature

3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1 h

4: 90 percent / aq. TiCl₃ / tetrahydrofuran / 1 h / Ambient temperature

With N-Bromosuccinimide; n-butyllithium; titanium(III) chloride; sodium; isopropyl alcohol; In tetrahydrofuran; water;

DOI:10.1248/cpb.45.759

upstream raw materials:

(R)-(+)-(E)-1-(p-toluenesulfinyl)-6,6,10-trimethyl-3,9-undecadien-2-one

Downstream raw materials:

(4aS,8aS)-(-)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-(p-toluenesulfenyl)-1H-2-benzopyran

(4aS,8aS,S_S)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-(p-toluenesulfinyl)-1H-2-benzopyran

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