(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

Base Information

• Chemical Name: (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
• CAS No.: 1353724-55-6
• Molecular Formula: C₃₀H₃₈O₃
• Molecular Weight: 446.63
• Mol file: 1353724-55-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 12 articles about (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 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: 96.0%

(4aS,6aS,11aR,11bS)-methyl-10-hydroxy-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluorene-7-carboxylate (1353724-47-6) + benzyl bromide (100-39-0) → (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)

Guidance literature:

With potassium carbonate; In acetone; for 12h; Inert atmosphere; Reflux;

DOI:10.1039/c1cc14608d

Reference yield:

sclareol (515-03-7) → (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)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; 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)-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)

Guidance literature:

Multi-step reaction with 8 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

With hydrogenchloride; 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)-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluoren-7-yl)methanol

(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