(1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol

Base Information

• Chemical Name: (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol
• CAS No.: 545374-99-0
• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.409
• Mol file: 545374-99-0.mol

Synonyms:(1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol

Chemical Property of (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol

There total 3 articles about (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-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: 88.0%

4-methoxybenzyl iodide (70887-29-5) + (1R,4aR,8aS)-cis-5-hydroxymethyl-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol (545375-33-5) → (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol (545374-99-0)

Guidance literature:

(1R,4aR,8aS)-cis-5-hydroxymethyl-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol; With sodium hydride; In N,N-dimethyl-formamide; at -60 ℃; for 0.25h;

4-methoxybenzyl iodide; In N,N-dimethyl-formamide; at -50 ℃; for 3h;

DOI:10.1002/hlca.200590078

Reference yield:

(4aS,8aR)-cis-4a-methyl-5-oxo-4a,5,8,8a-tetrahydro-naphthalene-1-carbaldehyde (862207-42-9) → (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol (545374-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.5 h / 0 °C

2.1: NaH / dimethylformamide / 0.25 h / -60 °C

2.2: 88 percent / dimethylformamide / 3 h / -50 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200590078

Reference yield:

(5S,6R)-5-acetyl-6-(2-ethoxyethenyl)-5-methylcyclohexa-1,3-diene-1-carboxaldehyde (545374-98-9) → (1R,4aR,8aS)-cis-5-(4-methoxy-benzyloxymethyl)-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol (545374-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / aq. HCl / tetrahydrofuran / Heating

2.1: 98 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.5 h / 0 °C

3.1: NaH / dimethylformamide / 0.25 h / -60 °C

3.2: 88 percent / dimethylformamide / 3 h / -50 °C

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200590078

upstream raw materials:

4-methoxybenzyl iodide

(1R,4aR,8aS)-cis-5-hydroxymethyl-8a-methyl-1,4,4a,8a-tetrahydronaphthalen-1-ol

(4aS,8aR)-cis-4a-methyl-5-oxo-4a,5,8,8a-tetrahydro-naphthalene-1-carbaldehyde

(5S,6R)-5-acetyl-6-(2-ethoxyethenyl)-5-methylcyclohexa-1,3-diene-1-carboxaldehyde

Downstream raw materials:

(2R,4aS,8aS)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-N,N-dimethylpropionamide

(3aS,4aS,8aS,9aS)-cis-5-(4-methoxy-benzyloxymethyl)-3,8a-dimethyl-3a,4,4a,8a,9,9a-hexahydro-3H-naphtho[2,3-b]furan-2-one

(3aS,4aR,8aS,9R,9aR)-cis-9-iodo-5-(4-methoxy-benzyloxymethyl)-3,8a-dimethyl-3a,4,4a,8a,9,9a-hexahydro-3H-naphtho[2,3-b]furan-2-one