(2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol

Base Information

• Chemical Name: (2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol
• CAS No.: 824940-65-0
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 824940-65-0.mol

Synonyms:(2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol

Chemical Property of (2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol

There total 2 articles about (2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol 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%

p-Anisaldehyde dimethyl acetal (2186-92-7) + (1S,3S)-2-hydroxymethyl-2-methylcyclohexane-1,3-diol (619335-74-9) → (2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol (824940-65-0)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol048010i

Reference yield:

(1S,3S)-2-benzyloxymethyl-2-methylcyclohexane-1,3-diol (619335-63-6) → (2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol (824940-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Raney Ni / 12 h / 20 °C

2: 90 percent / CSA / CH₂Cl₂ / 2 h / 20 °C

With camphor-10-sulfonic acid; hydrogen; nickel; In dichloromethane;

DOI:10.1021/ol048010i

Reference yield: 100.0%

(2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol (824940-65-0) + t-butyldimethylsiyl triflate (69739-34-0) → ((2R,4aS,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-yloxy)(tert-butyl)dimethylsilane (824940-80-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; at 20 ℃; for 1h;

DOI:10.1021/ol048010i

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(1S,3S)-2-hydroxymethyl-2-methylcyclohexane-1,3-diol

(1S,3S)-2-benzyloxymethyl-2-methylcyclohexane-1,3-diol

Downstream raw materials:

((2R,4aS,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-yloxy)(tert-butyl)dimethylsilane

[(1S,2S,6S)-2-(tert-butyldimethylsilanyloxy)-6-(4-methoxybenzyloxy)-1-methyl-cyclohexyl]methanol

(+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

((1S,2S,3S)-3-(4-methoxybenzyloxy)-2-(iodomethyl)-2-methylcyclohexyloxy)(tert-butyl)dimethylsilane