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

Base Information

Chemical Name:(1S,3R,4R,6R)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-cyclohexanecarbonitrile
CAS No.:272767-21-2
Molecular Formula:C₁₈H₂₅NO₃
Molecular Weight:303.401
Hs Code.:

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

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

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

There total 6 articles about (1S,3R,4R,6R)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-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: 40.0%

: 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

: 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

: (4aR,5S,7R,8S)-4a-cyano-8-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-5-isopropenyl-7,8-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one

Guidance literature:: With pyrrolidine; acetic acid; In tetrahydrofuran; toluene; for 0.5h; pH=5.2; Heating;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

: (4S,6R,7R)-7-(2R,3aS,6aR)-Hexahydro-furo[2,3-b]furan-2-yl-4-isopropenyl-6,7-dimethyl-4,5,6,7-tetrahydro-benzo[d]isoxazole

: 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

Guidance literature:: With sodium methylate; In methanol; diethyl ether; for 24h;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

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