labdanolic acid

Base Information

• Chemical Name: labdanolic acid
• CAS No.: 1891-82-3
• Molecular Formula: C₂₀H₃₆O₃
• Molecular Weight: 324.504
• Mol file: 1891-82-3.mol

Synonyms:

Chemical Property of labdanolic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of labdanolic acid

There total 10 articles about labdanolic 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: 75.0%

(+/-)-1β-<(3S)-4-cyano-3-methylbutyl>-2β,5,5,8aβ-tetramethyl-4aαH-decahydro-2α-naphthalenol (110259-70-6) → (+/-)-labdanolic acid (469-11-4,1891-81-2,1891-82-3,57538-23-5,86189-98-2,100194-81-8,110311-98-3,110311-99-4)

Guidance literature:

With dihydrogen peroxide; In sodium hydroxide; ethanol; water;

DOI:10.1248/cpb.34.3518

Reference yield:

(4aSR,8RS,8aRS)-8-hydroxy-1,4a,8a-trimethyl-4,4a,6,7,8,8a,9,10-octahydrophenanthren-2(3H)-one (72214-46-1) → (+/-)-labdanolic acid (469-11-4,1891-81-2,1891-82-3,57538-23-5,86189-98-2,100194-81-8,110311-98-3,110311-99-4)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium metal/liquid ammonia / tetrahydrofuran; liquid ammonia / 2 h / Heating

2: 95 percent / 80percent hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 1.) 170 deg C, 2 h; 2.) 230 deg C, 1 h

3: 98 percent / hydrogen / platinum oxide / acetic acid / 60 h / Ambient temperature

4: Jones reagent / acetone / 0.5 h / 0 °C

5: 61 percent / perbenzoic acid / CHCl₃ / 48 h / Ambient temperature

6: 72 percent / butyllithium/diisopropylamine / hexane; tetrahydrofuran / 2 h / Ambient temperature

7: lithium aluminium hydride / diethyl ether / 0.5 h / 0 °C

8: 87 percent / pyridine / 12 h / 0 °C

9: 93 percent / tributylamine / H₂O / 6 h / Heating

10: 75 percent / sodium hydroxide, 30percent hydrogen peroxide / H₂O; ethanol / 7.5 h / Heating

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; Perbenzoic acid; jones reagent; tributyl-amine; ammonia; hydrogen; dihydrogen peroxide; lithium; hydrazine hydrate; diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; chloroform; ammonia; water; acetic acid; acetone; diethylene glycol;

DOI:10.1246/bcsj.61.4023

Reference yield:

(+/-)-4bβ,8,8,10aβ-tetramethyl-1,2,3,4b,5,6,8,8aα,9,10,10a-dodecahydro-1β-phenanthrenol (110259-10-4) → (+/-)-labdanolic acid (469-11-4,1891-81-2,1891-82-3,57538-23-5,86189-98-2,100194-81-8,110311-98-3,110311-99-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / hydrogen / platinum oxide / acetic acid / 60 h / Ambient temperature

2: Jones reagent / acetone / 0.5 h / 0 °C

3: 61 percent / perbenzoic acid / CHCl₃ / 48 h / Ambient temperature

4: 72 percent / butyllithium/diisopropylamine / hexane; tetrahydrofuran / 2 h / Ambient temperature

5: lithium aluminium hydride / diethyl ether / 0.5 h / 0 °C

6: 87 percent / pyridine / 12 h / 0 °C

7: 93 percent / tributylamine / H₂O / 6 h / Heating

8: 75 percent / sodium hydroxide, 30percent hydrogen peroxide / H₂O; ethanol / 7.5 h / Heating

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; Perbenzoic acid; jones reagent; tributyl-amine; hydrogen; dihydrogen peroxide; diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; chloroform; water; acetic acid; acetone;

DOI:10.1246/bcsj.61.4023

upstream raw materials:

(+/-)-1β-<(3S)-4-cyano-3-methylbutyl>-2β,5,5,8aβ-tetramethyl-4aαH-decahydro-2α-naphthalenol

(4aSR,8RS,8aRS)-8-hydroxy-1,4a,8a-trimethyl-4,4a,6,7,8,8a,9,10-octahydrophenanthren-2(3H)-one

(+/-)-4bβ,8,8,10aβ-tetramethyl-4aαH,8aαH-tetradecahydro-1β-phenanthrenol

(+/-)-1β-<(3S)-4-hydroxy-3-methylbutyl>-2β,5,5,8aβ-tetramethyl-4aαH-decahydro-2α-naphthalenol

Downstream raw materials:

(+/-)-labdane-8α,15-diol

(3aR)-(+)-sclareolide

ambreinolide

(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-ol