(+)-atisirene

Base Information

• Chemical Name: (+)-atisirene
• CAS No.: 10178-85-5
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.474
• Mol file: 10178-85-5.mol

Synonyms:

Chemical Property of (+)-atisirene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-atisirene

There total 43 articles about (+)-atisirene 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:

(+)-(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethylnaphthalen-1-ol (110715-81-6) → (+)-atisirene (7721-78-0,10178-85-5,20230-48-2,21667-97-0,105018-17-5)

Guidance literature:

Multi-step reaction with 24 steps

1: 90 percent / Florisil, PCC / CH₂Cl₂ / 2 h / Ambient temperature

2: 97 percent / PBB / acetic acid / 2 h / Ambient temperature

3: 97 percent / sodium hydroxide / dimethylformamide; H₂O / 0.5 h / Ambient temperature

4: lead tetra-acetate (LTA) / benzene / 0.17 h / Ambient temperature

5: NaBH₄ / methanol / 0.33 h / Ambient temperature

6: 98 percent / tributylphosphine / tetrahydrofuran / 0.33 h / Ambient temperature

7: 91 percent / hydrogen peroxide / tetrahydrofuran / 10 h / Ambient temperature

8: 1.) lithium aluminium hydride; 2.) sodium hydroxide / 1.) diethyl ether, rt, 30 min; 2.) water, 30 min.

9: 88 percent / Florisil, PCC / CH₂Cl₂ / 1 h / Ambient temperature

10: 98 percent / toluene-p-sulphonic acid / benzene / 0.33 h / Heating

11: 1. osmium tetraoxide; 2.) sodium periodate / 1.) diethyl ether, water, rt, 5 min; 2.) rt, 10 h.

12: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C; 2.) THF, rt, 1 h.

13: 98 percent / H₂ / 10 percent palladium-charcoal / ethanol

15: 83 percent / 10 percent perchloric acid / tetrahydrofuran / 1 h / Ambient temperature

16: 47 percent / NaH / 1,2-dimethoxy-ethane / 72 h / Ambient temperature

17: 92 percent / LiHMDS / diethyl ether; hexane / 1.) -78 deg C, 1 h; 2.) rt, 1 h.

18: 100 percent / DIBAL / CH₂Cl₂ / 0.5 h / Ambient temperature

19: 59 percent / PDC / dimethylformamide / 3 h / Ambient temperature

20: 28 percent / TTPRCl / toluene / 2.5 h / Heating

21: 1.) LDA; 2.) bromine / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C, 0.5 h.

22: sodium borohydride / ethanol

23: zinc / ethanol / 1 h / Heating

With lead(IV) acetate; sodium hydroxide; sodium tetrahydroborate; florisil; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; perchloric acid; tributylphosphine; TTPRCl; hydrogen; dihydrogen peroxide; bromine; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; benzene;

Reference yield:

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6) → (+)-atisirene (7721-78-0,10178-85-5,20230-48-2,21667-97-0,105018-17-5)

Guidance literature:

Multi-step reaction with 23 steps

1: 97 percent / PBB / acetic acid / 2 h / Ambient temperature

2: 97 percent / sodium hydroxide / dimethylformamide; H₂O / 0.5 h / Ambient temperature

3: lead tetra-acetate (LTA) / benzene / 0.17 h / Ambient temperature

4: NaBH₄ / methanol / 0.33 h / Ambient temperature

5: 98 percent / tributylphosphine / tetrahydrofuran / 0.33 h / Ambient temperature

6: 91 percent / hydrogen peroxide / tetrahydrofuran / 10 h / Ambient temperature

7: 1.) lithium aluminium hydride; 2.) sodium hydroxide / 1.) diethyl ether, rt, 30 min; 2.) water, 30 min.

8: 88 percent / Florisil, PCC / CH₂Cl₂ / 1 h / Ambient temperature

9: 98 percent / toluene-p-sulphonic acid / benzene / 0.33 h / Heating

10: 1. osmium tetraoxide; 2.) sodium periodate / 1.) diethyl ether, water, rt, 5 min; 2.) rt, 10 h.

11: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C; 2.) THF, rt, 1 h.

12: 98 percent / H₂ / 10 percent palladium-charcoal / ethanol

14: 83 percent / 10 percent perchloric acid / tetrahydrofuran / 1 h / Ambient temperature

15: 47 percent / NaH / 1,2-dimethoxy-ethane / 72 h / Ambient temperature

16: 92 percent / LiHMDS / diethyl ether; hexane / 1.) -78 deg C, 1 h; 2.) rt, 1 h.

17: 100 percent / DIBAL / CH₂Cl₂ / 0.5 h / Ambient temperature

18: 59 percent / PDC / dimethylformamide / 3 h / Ambient temperature

19: 28 percent / TTPRCl / toluene / 2.5 h / Heating

20: 1.) LDA; 2.) bromine / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C, 0.5 h.

21: sodium borohydride / ethanol

22: zinc / ethanol / 1 h / Heating

With lead(IV) acetate; sodium hydroxide; sodium tetrahydroborate; florisil; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; perchloric acid; tributylphosphine; TTPRCl; hydrogen; dihydrogen peroxide; bromine; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; benzene;

Reference yield:

(-)-(1S,8aS)-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1-ol (110715-80-5) → (+)-atisirene (7721-78-0,10178-85-5,20230-48-2,21667-97-0,105018-17-5)

Guidance literature:

Multi-step reaction with 25 steps

1: 95 percent / H₂ / Adam's catalyst / acetic acid

2: 90 percent / Florisil, PCC / CH₂Cl₂ / 2 h / Ambient temperature

3: 97 percent / PBB / acetic acid / 2 h / Ambient temperature

4: 97 percent / sodium hydroxide / dimethylformamide; H₂O / 0.5 h / Ambient temperature

5: lead tetra-acetate (LTA) / benzene / 0.17 h / Ambient temperature

6: NaBH₄ / methanol / 0.33 h / Ambient temperature

7: 98 percent / tributylphosphine / tetrahydrofuran / 0.33 h / Ambient temperature

8: 91 percent / hydrogen peroxide / tetrahydrofuran / 10 h / Ambient temperature

9: 1.) lithium aluminium hydride; 2.) sodium hydroxide / 1.) diethyl ether, rt, 30 min; 2.) water, 30 min.

10: 88 percent / Florisil, PCC / CH₂Cl₂ / 1 h / Ambient temperature

11: 98 percent / toluene-p-sulphonic acid / benzene / 0.33 h / Heating

12: 1. osmium tetraoxide; 2.) sodium periodate / 1.) diethyl ether, water, rt, 5 min; 2.) rt, 10 h.

13: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C; 2.) THF, rt, 1 h.

14: 98 percent / H₂ / 10 percent palladium-charcoal / ethanol

16: 83 percent / 10 percent perchloric acid / tetrahydrofuran / 1 h / Ambient temperature

17: 47 percent / NaH / 1,2-dimethoxy-ethane / 72 h / Ambient temperature

18: 92 percent / LiHMDS / diethyl ether; hexane / 1.) -78 deg C, 1 h; 2.) rt, 1 h.

19: 100 percent / DIBAL / CH₂Cl₂ / 0.5 h / Ambient temperature

20: 59 percent / PDC / dimethylformamide / 3 h / Ambient temperature

21: 28 percent / TTPRCl / toluene / 2.5 h / Heating

22: 1.) LDA; 2.) bromine / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C, 0.5 h.

23: sodium borohydride / ethanol

24: zinc / ethanol / 1 h / Heating

With lead(IV) acetate; sodium hydroxide; sodium tetrahydroborate; florisil; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; perchloric acid; tributylphosphine; TTPRCl; hydrogen; dihydrogen peroxide; bromine; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; benzene;

upstream raw materials:

(+)-15-norisoatisirene

(16S)-ent-12β-p-Tolylsulfonyloxikauran

(13S,16S)-ent-Atisan-13-ol

(13R,16S)-ent-Atisan-13-ol