(1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

Base Information

• Chemical Name: (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene
• CAS No.: 343775-90-6
• Molecular Formula: C₂₇H₃₄O
• Molecular Weight: 374.566

Synonyms:(1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

Chemical Property of (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

There total 15 articles about (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene 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:

(3E,5E)-(R)-2-methyl-hepta-3,5-dienoic acid (343775-72-4) → (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene (343775-90-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 84 percent / DCC; HOBt / tetrahydrofuran / 20 °C

2.1: Pb(OAc)4 / ethyl acetate / 20 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 6 h / 20 °C / 760.05 Torr

4.1: 63 percent / K₂CO₃ / acetone / 24 h / Heating

5.1: 99 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / Heating

6.1: 96 percent / potassium carbonate / 1 h / 20 °C

7.1: 73 percent / diisobutylaluminium hydride / CH₂Cl₂; heptane / 1 h / 0 °C

8.1: 91 percent / aq. HCl / tetrahydrofuran / 48 h / 20 °C

9.1: aq. HCl; aq. NaNO₂ / tetrahydrofuran / 0.67 h / 0 °C

9.2: 91 percent / aq. NaCNBH₃ / tetrahydrofuran / 0 - 25 °C

10.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

11.1: t-BuOK / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.5 h / 0 °C

11.2: 96 percent / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.5 h / -20 °C

12.1: methanesulfonic acid / CH₂Cl₂ / 10 h / -78 - -40 °C

With lead(IV) acetate; hydrogenchloride; dmap; methanesulfonic acid; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; n-heptane; dichloromethane; ethyl acetate; acetone; 2.1: Diels-Alder reaction;

DOI:10.1021/ja010221k

Reference yield:

(R)-tert-butyl-dimethyl-(2-methyl-hepta-3,5-dienyloxy)-silane → (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene (343775-90-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2.1: 50 percent / chromium trioxide; conc. sulfuric acid / acetone; H₂O / 2 h / -10 °C

3.1: 84 percent / DCC; HOBt / tetrahydrofuran / 20 °C

4.1: Pb(OAc)4 / ethyl acetate / 20 °C

5.1: 100 percent / H₂ / Pd/C / methanol / 6 h / 20 °C / 760.05 Torr

6.1: 63 percent / K₂CO₃ / acetone / 24 h / Heating

7.1: 99 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / Heating

8.1: 96 percent / potassium carbonate / 1 h / 20 °C

9.1: 73 percent / diisobutylaluminium hydride / CH₂Cl₂; heptane / 1 h / 0 °C

10.1: 91 percent / aq. HCl / tetrahydrofuran / 48 h / 20 °C

11.1: aq. HCl; aq. NaNO₂ / tetrahydrofuran / 0.67 h / 0 °C

11.2: 91 percent / aq. NaCNBH₃ / tetrahydrofuran / 0 - 25 °C

12.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

13.1: t-BuOK / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.5 h / 0 °C

13.2: 96 percent / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.5 h / -20 °C

14.1: methanesulfonic acid / CH₂Cl₂ / 10 h / -78 - -40 °C

With chromium(VI) oxide; lead(IV) acetate; hydrogenchloride; dmap; methanesulfonic acid; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; n-heptane; dichloromethane; water; ethyl acetate; acetone; 4.1: Diels-Alder reaction;

DOI:10.1021/ja010221k

Reference yield:

(3E,5E)-(R)-2-methyl-hepta-3,5-dien-1-ol (220701-90-6) → (1S,3S,3aR,6R)-7-Benzyloxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene (343775-90-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 50 percent / chromium trioxide; conc. sulfuric acid / acetone; H₂O / 2 h / -10 °C

2.1: 84 percent / DCC; HOBt / tetrahydrofuran / 20 °C

3.1: Pb(OAc)4 / ethyl acetate / 20 °C

4.1: 100 percent / H₂ / Pd/C / methanol / 6 h / 20 °C / 760.05 Torr

5.1: 63 percent / K₂CO₃ / acetone / 24 h / Heating

6.1: 99 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / Heating

7.1: 96 percent / potassium carbonate / 1 h / 20 °C

8.1: 73 percent / diisobutylaluminium hydride / CH₂Cl₂; heptane / 1 h / 0 °C

9.1: 91 percent / aq. HCl / tetrahydrofuran / 48 h / 20 °C

10.1: aq. HCl; aq. NaNO₂ / tetrahydrofuran / 0.67 h / 0 °C

10.2: 91 percent / aq. NaCNBH₃ / tetrahydrofuran / 0 - 25 °C

11.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

12.1: t-BuOK / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.5 h / 0 °C

12.2: 96 percent / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.5 h / -20 °C

13.1: methanesulfonic acid / CH₂Cl₂ / 10 h / -78 - -40 °C

With chromium(VI) oxide; lead(IV) acetate; hydrogenchloride; dmap; methanesulfonic acid; sulfuric acid; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; n-heptane; dichloromethane; water; ethyl acetate; acetone; 3.1: Diels-Alder reaction;

DOI:10.1021/ja010221k

upstream raw materials:

(1R,4R)-5-Benzyloxy-1-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-4,7-dimethyl-1,2,3,4-tetrahydro-naphthalene

(3E,5E)-(R)-2-methyl-hepta-3,5-dienoic acid

(R)-2-((1R,4R)-5-Benzyloxy-4,7-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionaldehyde

(R)-2-((1R,4R)-5-Benzyloxy-4,7-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propan-1-ol

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