((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

Base Information

• Chemical Name: ((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
• CAS No.: 1353724-56-7
• Molecular Formula: C₂₉H₃₈O₂
• Molecular Weight: 418.62
• Mol file: 1353724-56-7.mol

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 14 articles about ((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 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: 93.0%

(4aS,6aS,11aR,11bS)-methyl 10-(benzyloxy)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorene-7-carboxylate (1353724-55-6) → ((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)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c1cc14608d

Reference yield:

sclareol (515-03-7) → ((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)

Guidance literature:

Multi-step reaction with 11 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

With hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; potassium tert-butylate; iodine; oxygen; lead(IV) tetraacetate; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; acetone; 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)-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)

Guidance literature:

Multi-step reaction with 9 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

With hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; potassium tert-butylate; iodine; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; acetone; 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

Downstream raw materials:

(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