(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

Base Information

Chemical Name:(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone
CAS No.:272767-26-7
Molecular Formula:C₁₅H₂₂O₄
Molecular Weight:266.337
Hs Code.:

Synonyms:(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

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Chemical Property of (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

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Technology Process of (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

There total 4 articles about (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone 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: 83.0%

: 272766-54-8
(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethylcyclohexanone

: 109-94-4
formic acid ethyl ester

: 272767-26-7
(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

Guidance literature:: With sodium hydride; In diethyl ether; at 20 ℃;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

: 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

: 272767-26-7
(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃ / methanol; CH₂Cl₂ / -78 °C

1.2: 82 percent / FeSO₄*7H₂O; Cu(OAc)2*2H₂O / methanol; CH₂Cl₂ / -78 - 20 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate

3.1: 83 percent / NaH / diethyl ether / 20 °C

With hydrogen; sodium hydride; ozone; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; ethyl acetate; 1.1: ozonolysis / 1.2: Oxidation / 2.1: Hydrogenation / 3.1: Formylation;
DOI:10.1016/S0040-4020(00)00110-1

Reference yield:

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

: 272767-26-7
(2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 4 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

3.1: 99 percent / H₂ / Pd/C / ethyl acetate

4.1: 83 percent / NaH / diethyl ether / 20 °C

With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; hydrogen; sodium hydride; ozone; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; ethyl acetate; 1.1: Methylation / 1.2: Mukaiyama reaction / 2.1: ozonolysis / 2.2: Oxidation / 3.1: Hydrogenation / 4.1: Formylation;
DOI:10.1016/S0040-4020(00)00110-1