(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

Base Information

Chemical Name:(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene
CAS No.:211053-83-7
Molecular Formula:C₂₄H₃₄O₄
Molecular Weight:386.532
Hs Code.:

Synonyms:(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

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Chemical Property of (-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

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Technology Process of (-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

There total 13 articles about (-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene 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:

: 59633-91-9,65754-93-0,108944-87-2,108944-88-3,136982-34-8,146611-16-7,807360-95-8
rac-12-nor-drimane-8α,11-diol

: 211053-83-7
(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

Guidance literature:: Multi-step reaction with 12 steps

1: 99 percent / conc. H₂SO₄ / dimethylsulfoxide / 1 h / Ambient temperature

2: 99 percent / p-dimethylaminopyridine, pyridine / 1 h / Ambient temperature

3: acylase I (Aspergillus melleus) / diisopropyl ether; H₂O / 48 h / 33 °C

4: 92 percent / H₂ / 20percent Pd(OH)2-C / methanol / Ambient temperature

5: conc. H₂SO₄ / dimethylsulfoxide / 0.5 h / Ambient temperature

6: LiAlH₄, AlCl₃ / diethyl ether / 0.5 h / -20 °C

7: CBr₄, Ph₃P / tetrahydrofuran / 0.25 h / Ambient temperature

8: H₂ / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature

9: 97 percent / CrO₃, H₂SO₄ / acetone / 0 °C

10: 86 percent / 1,8-diazabicyclo<5,4>undec-7-ene / benzene / 0.5 h / Ambient temperature

11: 1.) CuI / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

12: tetrahydrofuran / 0.33 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; acylase I (Aspergillus melleus); sulfuric acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; di-isopropyl ether; water; dimethyl sulfoxide; ethyl acetate; acetone; benzene;
DOI:10.1016/S0957-4166(98)00172-4

Reference yield:

: 190451-39-9,807360-95-8
(1R,2S,4aR,8aR)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthylmethanol

: 211053-83-7
(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

Guidance literature:: Multi-step reaction with 8 steps

1: conc. H₂SO₄ / dimethylsulfoxide / 0.5 h / Ambient temperature

2: LiAlH₄, AlCl₃ / diethyl ether / 0.5 h / -20 °C

3: CBr₄, Ph₃P / tetrahydrofuran / 0.25 h / Ambient temperature

4: H₂ / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature

5: 97 percent / CrO₃, H₂SO₄ / acetone / 0 °C

6: 86 percent / 1,8-diazabicyclo<5,4>undec-7-ene / benzene / 0.5 h / Ambient temperature

7: 1.) CuI / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

8: tetrahydrofuran / 0.33 h / Ambient temperature

With chromium(VI) oxide; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; sulfuric acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; ethyl acetate; acetone; benzene;
DOI:10.1016/S0957-4166(98)00172-4

Reference yield:

: 1-((3R,4aS,6aR,10aR,10bR)-7,7,10a-Trimethyl-decahydro-naphtho[2,1-d][1,3]dioxin-3-yl)-naphthalen-2-ol

: 211053-83-7
(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

Guidance literature:: Multi-step reaction with 11 steps

1: 99 percent / p-dimethylaminopyridine, pyridine / 1 h / Ambient temperature

2: acylase I (Aspergillus melleus) / diisopropyl ether; H₂O / 48 h / 33 °C

3: 92 percent / H₂ / 20percent Pd(OH)2-C / methanol / Ambient temperature

4: conc. H₂SO₄ / dimethylsulfoxide / 0.5 h / Ambient temperature

5: LiAlH₄, AlCl₃ / diethyl ether / 0.5 h / -20 °C

6: CBr₄, Ph₃P / tetrahydrofuran / 0.25 h / Ambient temperature

7: H₂ / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature

8: 97 percent / CrO₃, H₂SO₄ / acetone / 0 °C

9: 86 percent / 1,8-diazabicyclo<5,4>undec-7-ene / benzene / 0.5 h / Ambient temperature

10: 1.) CuI / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

11: tetrahydrofuran / 0.33 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; acylase I (Aspergillus melleus); sulfuric acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; di-isopropyl ether; water; dimethyl sulfoxide; ethyl acetate; acetone; benzene;
DOI:10.1016/S0957-4166(98)00172-4