(3aS,5S,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-5-hydroxy-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one

Base Information

Chemical Name:(3aS,5S,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-5-hydroxy-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one
CAS No.:68715-67-3
Molecular Formula:C₁₅H₂₀O₃
Molecular Weight:248.322
Hs Code.:
Mol file:68715-67-3.mol

Synonyms:Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11a-hexahydro-5-hydroxy-6,10-dimethyl-3-methylene-,[3aS-(3aR*,5R*,6E,10E,11aS*)]-; Haageanolide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3aS,5S,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-5-hydroxy-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one

Chemical Property:

PSA：46.53000
LogP:2.52160

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (3aS,5S,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-5-hydroxy-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one

There total 28 articles about (3aS,5S,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-5-hydroxy-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one 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: 70.0%

: 111723-73-0
(6E,10E)-(3aR,5R,11aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

: 68715-67-3,111819-80-8,126621-29-2
haagenolide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(01)87733-4

Reference yield:

: 1191-16-8
3-methylbut-2-enyl acetate

: 68715-67-3,111819-80-8,126621-29-2
haagenolide

Guidance literature:: Multi-step reaction with 22 steps

1: 1.) tert-butyl hydroperoxide, SeO₂, salicylic acid, 2.) NaBH₄ / 1.) water, CH₂Cl₂, 50h, RT, 2.) ethanol, 30 min

2: PPh₃, CBr₄ / acetonitrile / 0.25 h / 0 °C

3: 53 percent / K₂CO₃ / 0.5 h / 0 °C

4: 1.) p-toluenesulfonic acid, 2.) K₂CO₃ / 1.) CH₂Cl₂, 0 deg C, 3h, 2.) 30 min

5: KOH, tetrabutylammonium iodide / H₂O / 0.83 h

6: 1.) LiAlH₄, 2.) 30percent KOH / 1.) ether, 30 min

7: pyridine / 1 h / 0 °C

8: pyridinium p-toluenesulfonate (PPTS) / methanol / 3 h / 40 °C

9: 98.5 percent / CCl₄, PPh₃ / 12 h / Heating

10: K₂CO₃ / methanol / 0.5 h / 0 °C

11: 69 percent / MnO₂ / hexane / 20 h

12: KCN-dicyclohexyl-18-crown-6 / 0.5 h / Ambient temperature

13: benzyltrimethylammonium fluoride / 0.5 h

14: 95 percent / p-toluenesulfonic acid / benzene / 0.33 h / 0 °C

15: 80 percent / NaN(SiMe₃)2 / benzene; tetrahydrofuran

16: pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 40 °C

17: 99 percent / 1percent NaOH aq / diethyl ether / 0.08 h

18: diisobutylaluminium hydride / tetrahydrofuran; pentane / 0.08 h

19: 85 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

20: 1.) 1.5M sec-butyllithium, 2.) TMEDA / 1.) ether, cyclohexane, 30 min, -70 deg C, 2.) RT, 1h

21: MnO₂ / diethyl ether / 72 h / Ambient temperature

22: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; tetrachloromethane; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; carbon tetrabromide; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; salicylic acid; KCN*dicyclohexano-18-crown-6; pyridinium p-toluenesulfonate; trimethyl(benzyl)ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetonitrile; pentane; benzene;
DOI:10.1016/S0040-4020(01)87733-4

Reference yield:

: 37905-03-6
8-hydroxygeranyl acetate

: 68715-67-3,111819-80-8,126621-29-2
haagenolide

Guidance literature:: Multi-step reaction with 20 steps

1: pyridine / CH₂Cl₂ / 0.5 h

2: K₂CO₃ / methanol / 0.67 h / 0 °C

3: KOH, tetrabutylammonium iodide / H₂O / 0.83 h

4: 1.) LiAlH₄, 2.) 30percent KOH / 1.) ether, 30 min

5: pyridine / 1 h / 0 °C

6: pyridinium p-toluenesulfonate (PPTS) / methanol / 3 h / 40 °C

7: 98.5 percent / CCl₄, PPh₃ / 12 h / Heating

8: K₂CO₃ / methanol / 0.5 h / 0 °C

9: 69 percent / MnO₂ / hexane / 20 h

10: KCN-dicyclohexyl-18-crown-6 / 0.5 h / Ambient temperature

11: benzyltrimethylammonium fluoride / 0.5 h

12: 95 percent / p-toluenesulfonic acid / benzene / 0.33 h / 0 °C

13: 80 percent / NaN(SiMe₃)2 / benzene; tetrahydrofuran

14: pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 40 °C

15: 99 percent / 1percent NaOH aq / diethyl ether / 0.08 h

16: diisobutylaluminium hydride / tetrahydrofuran; pentane / 0.08 h

17: 85 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

18: 1.) 1.5M sec-butyllithium, 2.) TMEDA / 1.) ether, cyclohexane, 30 min, -70 deg C, 2.) RT, 1h

19: MnO₂ / diethyl ether / 72 h / Ambient temperature

20: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1H-imidazole; tetrachloromethane; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; KCN*dicyclohexano-18-crown-6; pyridinium p-toluenesulfonate; trimethyl(benzyl)ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1016/S0040-4020(01)87733-4