(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone

Base Information

Chemical Name:(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone
CAS No.:272766-99-1
Molecular Formula:C₁₄H₂₀O₃
Molecular Weight:236.311
Hs Code.:

Synonyms:(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone

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Chemical Property of (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone

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Technology Process of (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone

There total 2 articles about (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone 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: 82.0%

: 213833-81-9
(2R,3R,5R,2'R,3a'S,6a'R)-2-(hexahydrofuro[2,3-b]furan-2'-yl)-5-isopropenyl-2,3-dimethylcyclohexanone

: 272766-99-1
(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone

Guidance literature:: (2R,3R,5R,2'R,3a'S,6a'R)-2-(hexahydrofuro[2,3-b]furan-2'-yl)-5-isopropenyl-2,3-dimethylcyclohexanone; With ozone; In methanol; dichloromethane; at -78 ℃;

With copper diacetate; iron(II) sulfate; In methanol; dichloromethane; at -78 - 20 ℃;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

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

: 272766-99-1
(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone

Guidance literature:: Multi-step reaction with 2 steps

1.1: CuBr*Me₂S; TMSiCl

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

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: 82 percent / FeSO₄*7H₂O; Cu(OAc)2*2H₂O / methanol; CH₂Cl₂ / -78 - 20 °C

With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; ozone; In methanol; dichloromethane; 1.1: Methylation / 1.2: Mukaiyama reaction / 2.1: ozonolysis / 2.2: Oxidation;
DOI:10.1016/S0040-4020(00)00110-1