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

Base Information

Chemical Name:(4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone
CAS No.:213833-80-8
Molecular Formula:C₁₄H₂₀O₃
Molecular Weight:236.311
Hs Code.:

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

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

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

There total 12 articles about (4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone 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: 60.0%

: (5R,6S)-6-(2S,3aR,6aS)-Hexahydro-furo[2,3-b]furan-2-yl-5,6-dimethyl-3-phenylsulfanyl-cyclohex-2-enol

: 213833-80-8
(4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone

Guidance literature:: With toluene-4-sulfonic acid; In various solvent(s);
DOI:10.1016/S0040-4039(98)01367-7

Reference yield:

: 213833-70-6
(3R,5R)-(5-isopropenyl-2,3-dimethylcyclohex-1-enyloxy)trimethylsilane

: 213833-80-8
(4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 40 percent / triphenylmethyl perchlorate / CH₂Cl₂ / 78 h / -78 °C

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

2.2: 70 percent / FeSO₄*7H₂O; Cu(OAc)2*H₂O / CH₂Cl₂; methanol / -78 - 20 °C

3.1: 73 percent / Et₃N / pentane; tetrahydrofuran / 27 h

4.1: 93 percent / trichloroisocyanuric acid / diethyl ether; benzene / 0.08 h / 0 °C

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

6.1: 4.2 g / PTSA / CHCl₃

With lithium aluminium tetrahydride; trityl perchlorate; trichloroisocyanuric acid; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; pentane; benzene; 1.1: Mukaiyama addition / 2.1: ozonolysis / 2.2: Elimination / 3.1: Addition / 4.1: Chlorination / 5.1: Reduction / 6.1: Hydrolysis;
DOI:10.1021/jo991151r

Reference yield:

: (2R,3R)-2-(2S,3aR,6aS)-Hexahydro-furo[2,3-b]furan-2-yl-2,3-dimethyl-5-phenylsulfanyl-cyclohexanone

: 213833-80-8
(4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / trichloroisocyanuric acid / diethyl ether; benzene / 0.08 h / 0 °C

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

3: 4.2 g / PTSA / CHCl₃

With lithium aluminium tetrahydride; trichloroisocyanuric acid; toluene-4-sulfonic acid; In diethyl ether; chloroform; benzene; 1: Chlorination / 2: Reduction / 3: Hydrolysis;
DOI:10.1021/jo991151r