(6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

Base Information

Chemical Name:(6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione
CAS No.:84066-38-6
Molecular Formula:C₂₂H₂₆O₅
Molecular Weight:370.445
Hs Code.:

Synonyms:(6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

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Chemical Property of (6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

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Technology Process of (6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

There total 7 articles about (6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione 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: 70.0%

: 84066-37-5
(6E,10Z)-(3aR,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

: 84066-38-6
(6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 25 ℃; for 3h;
DOI:10.1021/ja00341a055

Reference yield:

: (3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-diene-2,11-dione

: 84066-38-6
(6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: H₂O₂, Ti(O-i-Pr)4, i-Pr₂NEt / diethyl ether / 0.25 h / -30 °C

2: NaBH₄ / methanol / 0.5 h / 0 °C

3: 61 percent / K₂CO₃ / methanol / 5 h / 25 °C

4: 71 percent / Collins reagent / CH₂Cl₂ / 0.08 h / 25 °C

5: 70 percent / DBU / tetrahydrofuran / 3 h / 25 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; Collins oxidation agent; dihydrogen peroxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja00341a055

Reference yield:

: 84066-36-4
(5Z,9E)-(3aR,4S,7S,11aS)-7-Benzyloxymethoxy-4-hydroxy-6,10-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one

: 84066-38-6
(6E,10Z)-(3aS,9S,11aS)-9-Benzyloxymethoxy-6,10-dimethyl-3,3a,5,8,9,11a-hexahydro-cyclodeca[b]furan-2,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 61 percent / K₂CO₃ / methanol / 5 h / 25 °C

2: 71 percent / Collins reagent / CH₂Cl₂ / 0.08 h / 25 °C

3: 70 percent / DBU / tetrahydrofuran / 3 h / 25 °C

With Collins oxidation agent; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00341a055