(20ξ)-5α-Dammara-24-ene-3β,20-diol

Base Information

• Chemical Name: (20ξ)-5α-Dammara-24-ene-3β,20-diol
• CAS No.: 19132-83-3
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 444.742
• Mol file: 19132-83-3.mol

Synonyms:

Chemical Property of (20ξ)-5α-Dammara-24-ene-3β,20-diol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20ξ)-5α-Dammara-24-ene-3β,20-diol

There total 74 articles about (20ξ)-5α-Dammara-24-ene-3β,20-diol 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: 100.0%

(R)-2-[(3S,5R,9S,10R,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-en-2-ol (128685-91-6,128777-75-3,136734-43-5,136735-34-7) → (3S,5R,9S,10R,13S,14S,17R)-17-((R)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol (14351-28-1,14351-29-2,19132-83-3,33426-07-2,53368-74-4,59686-24-7,111956-30-0,114926-01-1,128777-74-2,136734-44-6,136734-47-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 10h;

Reference yield: 100.0%

(S)-2-[(3S,5R,9S,10R,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-en-2-ol (128685-91-6,128777-75-3,136734-43-5,136735-34-7) → (3S,5R,9S,10R,13S,14S,17R)-17-((S)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol (14351-28-1,14351-29-2,19132-83-3,33426-07-2,53368-74-4,59686-24-7,111956-30-0,114926-01-1,128777-74-2,136734-44-6,136734-47-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 10h;

Reference yield:

2-methylcyclohexane-1,3-dione (1193-55-1) → (3S,5R,9S,10R,13S,14S,17R)-17-((R)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol (14351-28-1,14351-29-2,19132-83-3,33426-07-2,53368-74-4,59686-24-7,111956-30-0,114926-01-1,128777-74-2,136734-44-6,136734-47-9)

Guidance literature:

Multi-step reaction with 28 steps

1: Et₃N / 1,2-dimethoxy-ethane / 23 °C

2: (S)-phenylalanine, (+)-camphorsulfonic acid / dimethylformamide / 576 h / 23 °C

3: 1.) potassium hexamethyldisilazide, Et₃B / 1.) THF, -78 deg C, 2.) -25 deg C, 2 h

4: HgCl₂, water, pyridine / tetrahydrofuran / 36 h / 23 °C

5: Cs₂CO₃ / tetrahydrofuran / 16 h / 23 °C

6: 77 percent / lithium trisiamylborohydride / tetrahydrofuran / -40 °C

7: 1.) n-BuLi / 1.) ether, -20 deg C, 2.) 23 deg C, 12 h

8: 94 percent / C₆H₅NMe₂ / 1 h / 20 °C

9: 1.) Li, liquid NH₃, water / 1.) THF, -40 deg C, 3 min, 2.) -70 deg C, 1 h

10: 0.02percent aq. HCl / acetone / 20 h / 23 °C

11: 1percent aq. KOH / methanol / 6 h / Heating

12: 100 percent / sodium borohydride / tetrahydrofuran; methanol / 1 h / 0 °C

14: 97 percent / methylmagnesium isopropylcyclohexylamide / diethyl ether; toluene / 12 h / 4 °C

15: periodinane / CH₂Cl₂ / 1 h / 23 °C

16: 1.) Li, liquid NH₃, water / 1.) THF, -40 deg C, 3 min, 2.) 30 min

17: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 0 °C

18: 98 percent / imidazole / dimethylformamide / 12 h / 50 °C

19: 94 percent / diphenylbromoborane / CH₂Cl₂ / 0.17 h / -40 °C

20: 95 percent / pyridinium chlorochromate on Al₂O₃ / CH₂Cl₂ / 5 h / 23 °C

22: 92 percent / Li, liquid NH₃, water / tetrahydrofuran / 0.67 h / -50 °C

23: 1.) n-BuLi / 1.) THF, -20 deg C, 2.) 23 deg C, 2 h

24: Li, EtNH₂ / 2-methyl-propan-2-ol / 0.5 h / 0 °C

25: 95 percent / 1percent CF₃CO₂H / tetrahydrofuran; H₂O / 3 h / 23 °C

26: 93 percent / pyridinium chlorochromate on Al₂O₃ / CH₂Cl₂ / 5 h / 20 °C

27: 30 percent / diethyl ether / 0.5 h / 0 °C

28: 100 percent / Bu₄NF / tetrahydrofuran / 10 h / 50 °C

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; triethyl borane; L-phenylalanine; pyridiniumchlorochromate on aluminumoxide; bromodiphenylborane; tetrabutyl ammonium fluoride; ammonia; water; lithium; potassium hexamethylsilazane; methylmagnesium N-cyclohexylisopropylamide; caesium carbonate; Dess-Martin periodane; ethylamine; N,N-dimethyl-aniline; (+)-10-camphorsulfonic acid; lithium tri-sec-butyl(hydrido)borate; triethylamine; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

upstream raw materials:

20-ξ(2)-Hydroxy-3-oxo-dammaren-(24); Dipterocarpol

(R)-2-[(3S,5R,9S,10R,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-en-2-ol

2-methylcyclohexane-1,3-dione

6-(2-ethyl-[1,3]dioxolan-2-yl)-hex-1-en-3-one

Downstream raw materials:

1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

1-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Trifluoro-methanesulfonic acid 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-vinyl ester

C₅₅H₈₂N₂O₃SSi