Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester
• CAS No.: 81522-26-1
• Molecular Formula: C₁₇H₂₇BrO₂
• Molecular Weight: 343.304
• Mol file: 81522-26-1.mol

Synonyms:Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester

Chemical Property of Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester

There total 2 articles about Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester 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: 12.0%

(2E,6E)-farnesyl acetate (4128-17-0) → Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester (81522-26-1) + rac-(E)-5-((1S,3R)-3-bromo-2,2-dimethyl-6-methylenecyclohexyl)-3-methylpent-2-en-1-yl acetate (81517-82-0) + Acetic acid (E)-(S)-6-bromo-6-((2R,5S)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-3-methyl-hex-2-enyl ester (81517-83-1)

Guidance literature:

With N-Bromosuccinimide; In water; acetone; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(01)92422-0

Reference yield: 8.0%

(2E,6E)-farnesyl acetate (4128-17-0) → Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester (81522-26-1) + rac-(E)-5-((1S,3R)-3-bromo-2,2-dimethyl-6-methylenecyclohexyl)-3-methylpent-2-en-1-yl acetate (81517-82-0)

Guidance literature:

With N-Bromosuccinimide; In acetic acid; tert-butyl alcohol; at 0 ℃; for 24h;

DOI:10.1016/S0040-4039(01)92422-0

Reference yield:

Acetic acid (1S,4aR,6S,8aS)-6-bromo-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester (81522-26-1) → C25H36Br2O5

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; methanol / 1 h / 50 °C / Inert atmosphere

1.2: 25 °C / Cooling with ice

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexanes / 0.33 h / -78 °C / Inert atmosphere

3.2: 0.33 h / -40 °C / Inert atmosphere

With methanol; n-butyllithium; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; hexanes; dichloromethane;

upstream raw materials:

(2E,6E)-farnesyl acetate

Downstream raw materials:

C₂₂H₂₉BrO₃