(4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene

Base Information

Chemical Name:(4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene
CAS No.:211053-91-7
Molecular Formula:C₂₁H₃₁BrO
Molecular Weight:379.381
Hs Code.:

Synonyms:

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Chemical Property of (4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene

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Technology Process of (4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene

There total 8 articles about (4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene 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

: 211053-91-7
(4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene

Guidance literature:: Multi-step reaction with 7 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

With pyridine; dmap; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; acylase I (Aspergillus melleus); sulfuric acid; hydrogen; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; di-isopropyl ether; water; dimethyl sulfoxide;
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

: 211053-91-7
(4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene

Guidance literature:: Multi-step reaction with 6 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

With pyridine; dmap; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; acylase I (Aspergillus melleus); sulfuric acid; hydrogen; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; di-isopropyl ether; water; dimethyl sulfoxide;
DOI:10.1016/S0957-4166(98)00172-4

Reference yield:

: 8-((3R,4aS,6aR,10aR,10bR)-7,7,10a-Trimethyl-decahydro-naphtho[2,1-d][1,3]dioxin-3-yl)-naphthalen-1-ol

: 211053-91-7
(4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / H₂ / 20percent Pd(OH)2-C / methanol / Ambient temperature

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

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

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

With lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; sulfuric acid; hydrogen; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide;
DOI:10.1016/S0957-4166(98)00172-4