(4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine

Base Information

• Chemical Name: (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine
• CAS No.: 1353724-57-8
• Molecular Formula: C₃₀H₄₀O₂
• Molecular Weight: 432.646
• Mol file: 1353724-57-8.mol

Synonyms:(4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine

Chemical Property of (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine

There total 15 articles about (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine 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: 98.0%

((4aS,6aS,11aR,11bS)-10-(benzyloxy)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluoren-7-yl)methanol (1353724-56-7) → (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine (1353724-57-8)

Guidance literature:

((4aS,6aS,11aR,11bS)-10-(benzyloxy)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluoren-7-yl)methanol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.0833333h; Inert atmosphere;

With methyl iodide; In tetrahydrofuran; mineral oil; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c1cc14608d

Reference yield:

sclareol (515-03-7) → (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine (1353724-57-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: oxygen; lead(IV) tetraacetate; ozone / dichloromethane / 5 h / 0 °C / Inert atmosphere

2.1: collidine / 10 h / 180 °C / Inert atmosphere

3.1: iodine / dichloromethane / 5 h / 20 °C / Inert atmosphere

4.1: borane-THF / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

4.2: 5 h / 0 - 20 °C / Inert atmosphere

5.1: dipyridinium dichromate / dichloromethane / 10 h / 20 °C / Inert atmosphere

6.1: potassium tert-butylate / benzene / 2 h / 20 °C / Inert atmosphere

7.1: hydrogenchloride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

9.1: 5,5-dimethyl-1,3-cyclohexadiene / 72 h / 150 °C / Inert atmosphere

9.2: 3 h / 100 °C / Inert atmosphere

10.1: potassium carbonate / acetone / 12 h / Inert atmosphere; Reflux

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

12.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C / Inert atmosphere

12.2: 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; potassium tert-butylate; iodine; oxygen; lead(IV) tetraacetate; sodium hydride; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; acetone; mineral oil; benzene; 7.1: Aldol condensation / 9.2: Diels-Alder reaction;

DOI:10.1039/c1cc14608d

Reference yield:

4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one (10266-75-8) → (4aS,6aS,11aR,11bS)-10-(benzyloxy)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorine (1353724-57-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: iodine / dichloromethane / 5 h / 20 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

2.2: 5 h / 0 - 20 °C / Inert atmosphere

3.1: dipyridinium dichromate / dichloromethane / 10 h / 20 °C / Inert atmosphere

4.1: potassium tert-butylate / benzene / 2 h / 20 °C / Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: 5,5-dimethyl-1,3-cyclohexadiene / 72 h / 150 °C / Inert atmosphere

7.2: 3 h / 100 °C / Inert atmosphere

8.1: potassium carbonate / acetone / 12 h / Inert atmosphere; Reflux

9.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

10.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C / Inert atmosphere

10.2: 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; potassium tert-butylate; iodine; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; acetone; mineral oil; benzene; 5.1: Aldol condensation / 7.2: Diels-Alder reaction;

DOI:10.1039/c1cc14608d

upstream raw materials:

((1S,2S,4aS,8aR)-5,5,8a-trimethyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)decahydronaphthalen-2-yl)methanol

(1S,2S,4aS,8aR)-5,5,8a-trimethyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)decahydronaphthalene-2-carbaldehyde

(1R,2S,4aS,8aS)-2,5,5,8a-tetramethyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)decahydronaphthalene-2-carbaldehyde

1-((3aR,5aS,9aS,9bS)-3a,6,6,9a-tetramethyl-3a,4,5,5a,6,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-2-yl)ethanone