(3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone

Base Information

• Chemical Name: (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone
• CAS No.: 254752-73-3
• Molecular Formula: C₁₉H₃₀O₃
• Molecular Weight: 306.445

Synonyms:(3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone

Chemical Property of (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone

There total 13 articles about (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone 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: 88.0%

4-penten-1-ylmagnesium bromide (34164-50-6) + (4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone (213833-80-8) → (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone (254752-73-3)

Guidance literature:

With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; at -78 ℃; for 5h;

DOI:10.1021/jo991151r

Reference yield:

hexahydro furo<2,3-b>furan-2-one (104223-37-2) → (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone (254752-73-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: DIBALH / toluene / 1.5 h / -78 °C

1.2: 62 percent / BF₃*Et₂O / toluene / 0.08 h / -78 - -60 °C

2.1: 40 percent / triphenylmethyl perchlorate / CH₂Cl₂ / 78 h / -78 °C

3.1: ozone / CH₂Cl₂; methanol / -78 °C

3.2: 70 percent / FeSO₄*7H₂O; Cu(OAc)2*H₂O / CH₂Cl₂; methanol / -78 - 20 °C

4.1: 73 percent / Et₃N / pentane; tetrahydrofuran / 27 h

5.1: 93 percent / trichloroisocyanuric acid / diethyl ether; benzene / 0.08 h / 0 °C

6.1: LiAlH₄ / diethyl ether / 0.5 h / 20 °C

7.1: 4.2 g / PTSA / CHCl₃

8.1: 88 percent / CuBr*Me₂S; TMSCl / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 5 h / -78 °C

With lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; trityl perchlorate; trichloroisocyanuric acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; chloroform; toluene; pentane; benzene; 1.1: Reduction / 1.2: Etherification / 2.1: Mukaiyama addition / 3.1: ozonolysis / 3.2: Elimination / 4.1: Addition / 5.1: Chlorination / 6.1: Reduction / 7.1: Hydrolysis / 8.1: Addition;

DOI:10.1021/jo991151r

Reference yield:

(+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol (100460-14-8) → (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone (254752-73-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 88 percent / pyridine / CHCl₃ / 2 h

2.1: 81 percent / dimethylformamide / 18 h / 70 °C

3.1: aq. NaOH / 2.5 h / Heating

3.2: 91 percent / aq. HCl / 1.5 h / 20 °C / pH 1

4.1: DIBALH / toluene / 1.5 h / -78 °C

4.2: 62 percent / BF₃*Et₂O / toluene / 0.08 h / -78 - -60 °C

5.1: 40 percent / triphenylmethyl perchlorate / CH₂Cl₂ / 78 h / -78 °C

6.1: ozone / CH₂Cl₂; methanol / -78 °C

6.2: 70 percent / FeSO₄*7H₂O; Cu(OAc)2*H₂O / CH₂Cl₂; methanol / -78 - 20 °C

7.1: 73 percent / Et₃N / pentane; tetrahydrofuran / 27 h

8.1: 93 percent / trichloroisocyanuric acid / diethyl ether; benzene / 0.08 h / 0 °C

9.1: LiAlH₄ / diethyl ether / 0.5 h / 20 °C

10.1: 4.2 g / PTSA / CHCl₃

11.1: 88 percent / CuBr*Me₂S; TMSCl / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 5 h / -78 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; trityl perchlorate; trichloroisocyanuric acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; pentane; benzene; 1.1: Tosylation / 2.1: Substitution / 3.1: Hydrolysis / 3.2: Cyclization / 4.1: Reduction / 4.2: Etherification / 5.1: Mukaiyama addition / 6.1: ozonolysis / 6.2: Elimination / 7.1: Addition / 8.1: Chlorination / 9.1: Reduction / 10.1: Hydrolysis / 11.1: Addition;

DOI:10.1021/jo991151r

upstream raw materials:

4-penten-1-ylmagnesium bromide

(4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone

(+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol

hexahydro furo<2,3-b>furan-2-one

Downstream raw materials:

(1R,2S,3R,2'S,3a'R,6a'S)-4-(4-(hexahydrofuro[2,3-b]furan-2'-yl)-2,3-dimethyl-5-oxocyclohexyl)butyraldehyde

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