(1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

Base Information

Chemical Name:(1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile
CAS No.:272766-70-8
Molecular Formula:C₂₂H₃₁NO₄
Molecular Weight:373.492
Hs Code.:

Synonyms:(1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

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Chemical Property of (1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

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Technology Process of (1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

There total 6 articles about (1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile 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: 95.0%

: 78-94-4,25038-87-3
methyl vinyl ketone

: 272767-21-2
(1S,3R,4R,6R)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-cyclohexanecarbonitrile

: 272766-70-8
(1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

Guidance literature:: With sodium methylate; In methanol; benzene; for 456h;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

: 6485-40-1,2244-16-8
(R)-Carvone

: 272766-70-8
(1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: CuBr*Me₂S; TMSiCl

1.2: 35 percent / TrSbCl₆ / CH₂Cl₂ / -78 °C

2.1: 95 percent / NaH / diethyl ether / 20 °C

3.1: NH₂OH*HCl; NaOAc / ethanol; CHCl₃ / 48 h

4.1: NaOMe / methanol; diethyl ether / 24 h

5.1: 95 percent / NaOMe / benzene; methanol / 456 h

With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; hydroxylamine hydrochloride; sodium methylate; sodium acetate; sodium hydride; In methanol; diethyl ether; ethanol; chloroform; benzene; 1.1: Methylation / 1.2: Mukaiyama reaction / 2.1: Formylation / 3.1: Condensation / 4.1: Ring cleavage / 5.1: Michael addition;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

: 213833-82-0
(+/-)-2-methoxyhexahydrofuro[2,3-b]furan

: 272766-70-8
(1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: CuBr*Me₂S; TMSiCl

1.2: 35 percent / TrSbCl₆ / CH₂Cl₂ / -78 °C

2.1: 95 percent / NaH / diethyl ether / 20 °C

3.1: NH₂OH*HCl; NaOAc / ethanol; CHCl₃ / 48 h

4.1: NaOMe / methanol; diethyl ether / 24 h

5.1: 95 percent / NaOMe / benzene; methanol / 456 h

With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; hydroxylamine hydrochloride; sodium methylate; sodium acetate; sodium hydride; In methanol; diethyl ether; ethanol; chloroform; benzene; 1.1: Methylation / 1.2: Mukaiyama reaction / 2.1: Formylation / 3.1: Condensation / 4.1: Ring cleavage / 5.1: Michael addition;
DOI:10.1016/S0040-4020(00)00110-1