(1S,8aβ)-Decahydro-5α-[(E)-5-hydroxy-3-methyl-3-pentenyl]-1,4aα-dimethyl-6-methylene-1-naphthalenecarboxylic acid

Base Information

• Chemical Name: (1S,8aβ)-Decahydro-5α-[(E)-5-hydroxy-3-methyl-3-pentenyl]-1,4aα-dimethyl-6-methylene-1-naphthalenecarboxylic acid
• CAS No.: 77096-82-3
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Mol file: 77096-82-3.mol

Synonyms:isocupressic acid;viscidic acid A;(1S,4aS,5R,8aS)-5-((E)-5-Hydroxy-3-methyl-pent-3-enyl)-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid;

Chemical Property of (1S,8aβ)-Decahydro-5α-[(E)-5-hydroxy-3-methyl-3-pentenyl]-1,4aα-dimethyl-6-methylene-1-naphthalenecarboxylic acid

Chemical Property:

• PSA: 57.53000
• LogP: 4.56870

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,8aβ)-Decahydro-5α-[(E)-5-hydroxy-3-methyl-3-pentenyl]-1,4aα-dimethyl-6-methylene-1-naphthalenecarboxylic acid

There total 1 articles about (1S,8aβ)-Decahydro-5α-[(E)-5-hydroxy-3-methyl-3-pentenyl]-1,4aα-dimethyl-6-methylene-1-naphthalenecarboxylic acid 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:

cryptomeridiol-4-yl-19-acetoxylabda-8(17),13E-dien-19-oate → isocupressic acid (69308-72-1,77096-82-3,1909-91-7) + cryptomeridiol (55353-16-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1016/S0031-9422(00)89538-2

Reference yield: 91.0%

benzyl bromide (100-39-0) + isocupressic acid (69308-72-1,77096-82-3,1909-91-7) → C27H38O3

Guidance literature:

With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201602476

Reference yield:

isocupressic acid (69308-72-1,77096-82-3,1909-91-7) → strongylophorine 8

Guidance literature:

Multi-step reaction with 11 steps

1.1: potassium carbonate / dichloromethane; N,N-dimethyl-formamide / 24 h / 0 °C / Inert atmosphere

2.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 24.5 h / 0 - 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C / 760.05 Torr / Inert atmosphere

5.1: ammonium bicarbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole; triethylamine / dichloromethane; N,N-dimethyl-formamide / 72 h / 0 - 20 °C / Inert atmosphere

6.1: iodine; lead(IV) tetraacetate / benzene / 20 h / 20 °C / Irradiation; Inert atmosphere

7.1: potassium hydroxide / methanol / 2 h / Reflux; Inert atmosphere

8.1: hydrogenchloride / acetonitrile; water / 4 h / 100 °C / Reflux; Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen; acetic acid / ethyl acetate / 12 h / 40 °C / Inert atmosphere

10.1: sodium iodide; chloro-trimethyl-silane / toluene; acetonitrile / 18 h / 40 °C / Inert atmosphere

11.1: oxygen / dichloromethane / 0.5 h / 20 °C / 760.05 Torr / Inert atmosphere

11.2: 1 h / 20 °C / 760.05 Torr / Inert atmosphere

With hydrogenchloride; chloro-trimethyl-silane; 1-hydroxy-7-aza-benzotriazole; tributylphosphine; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; iodine; oxygen; lead(IV) tetraacetate; ammonium bicarbonate; potassium carbonate; acetic acid; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium iodide; potassium hydroxide; 1,1'-azodicarbonyl-dipiperidine; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/anie.201602476

Downstream raw materials:

viscidic acid B

acetyl isocupressic acid

agathic acid

dihydroagathic acid

Refernces