(1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

Base Information

• Chemical Name: (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol
• CAS No.: 196805-86-4
• Molecular Formula: C₂₃H₃₆O₂
• Molecular Weight: 344.538
• Mol file: 196805-86-4.mol

Synonyms:(1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

Chemical Property of (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

There total 18 articles about (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-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:

3,5,6,7,8,8a-hexahydro-5,5,8aβ-trimethylnaphthalen-2(1H)-one (123298-84-0) → (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol (196805-86-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating

2: 1.) LDA / 1.) THF, from 0 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

3: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature

4: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C

5: 92 percent / LiAlH₄ / diethyl ether / 0.17 h / Ambient temperature

6: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 2.) THF, reflux, 22 h

7: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature

8: 1.) CeCl₃ / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min

With hydrogenchloride; lithium aluminium tetrahydride; cerium(III) chloride; trifluorormethanesulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetone;

DOI:10.1139/v97-136

Reference yield:

4aα,5,6,7,8,8a-hexahydro-5,5,8aβ-trimethyl-2-oxo-1α-naphthalene acetic acid ethyl ester (196805-74-0) → (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol (196805-86-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature

2: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C

3: 92 percent / LiAlH₄ / diethyl ether / 0.17 h / Ambient temperature

4: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 2.) THF, reflux, 22 h

5: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature

6: 1.) CeCl₃ / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min

With hydrogenchloride; lithium aluminium tetrahydride; cerium(III) chloride; trifluorormethanesulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetone;

DOI:10.1139/v97-136

Reference yield:

2,3,4,4a,5,6,7,8-octahydro-2β,3α-dihydroxy-4aβ,8,8-trimethylnaphthalene (196805-72-8) → (1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol (196805-86-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 13 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating

2: 65 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating

3: 1.) LDA / 1.) THF, from 0 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

4: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature

5: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C

6: 92 percent / LiAlH₄ / diethyl ether / 0.17 h / Ambient temperature

7: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 2.) THF, reflux, 22 h

8: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature

9: 1.) CeCl₃ / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min

With hydrogenchloride; lithium aluminium tetrahydride; cerium(III) chloride; trifluorormethanesulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetone;

DOI:10.1139/v97-136

upstream raw materials:

methyllithium

(1R,4aS,8aS)-1-(2-Benzyloxy-ethyl)-5,5,8a-trimethyl-octahydro-naphthalen-2-one

benzyl bromide

benzyl chloride

Downstream raw materials:

(-)-ambroxide

13,14,15,16-tetranor-8βH-labdane-8,12-diol

Refernces