(3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene

Base Information

• Chemical Name: (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene
• CAS No.: 157519-04-5
• Molecular Formula: C₂₁H₃₀O
• Molecular Weight: 298.469
• Mol file: 157519-04-5.mol

Synonyms:(3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene

Chemical Property of (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene

There total 6 articles about (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro 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: 69.0%

benzyl bromide (100-39-0) + 2α-hydroxy-1,1,4a(R),6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene (151702-17-9) → (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene (157519-04-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 23 ℃; for 3h;

DOI:10.1016/S0040-4039(00)73036-X

Reference yield:

3,11-dioxoolean-12-en-30-oic acid (6184-16-3,7020-50-0,146236-29-5) → (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene (157519-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide (BMPS) / 3 h / 350 °C / 40 Torr

2: NaBH₄ / methanol / -78 °C

3: NaH / dimethylformamide / 2 h / 25 °C

With sodium tetrahydroborate; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja00077a073

Reference yield:

(4aR)-2-oxo-1.1.4a.6-tetramethyl-trans-1.2.3.4.4a.7.8.8a-octahydro-naphthalene (151702-16-8) → (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene (157519-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / -78 °C

2: NaH / dimethylformamide / 2 h / 25 °C

With sodium tetrahydroborate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja00077a073

upstream raw materials:

benzyl bromide

2α-hydroxy-1,1,4a(R),6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene

3,11-dioxoolean-12-en-30-oic acid

(4aR)-2-oxo-1.1.4a.6-tetramethyl-trans-1.2.3.4.4a.7.8.8a-octahydro-naphthalene

Downstream raw materials:

(4aR,4bS,7S,8aR,10aR)-7-Benzyloxy-4b,8,8,10a-tetramethyl-1-phenylsulfanyl-dodecahydro-phenanthren-2-one

(3aR,5aR,7S,9aS,9bR)-7-Benzyloxy-3a,6,6,9a-tetramethyl-dodecahydro-cyclopenta[a]naphthalen-3-one

(3S,4aR,8aS)-3-Benzyloxy-4,4,7,8a-tetramethyl-8-vinyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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