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

Base Information

Chemical Name:(6E,10Z)-(3aR,4R,9S,11aS)-9-Benzyloxymethoxy-4-hydroxy-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
CAS No.:84066-39-7
Molecular Formula:C₂₂H₂₈O₅
Molecular Weight:372.461
Hs Code.:

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

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

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

There total 8 articles about (6E,10Z)-(3aR,4R,9S,11aS)-9-Benzyloxymethoxy-4-hydroxy-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one 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: 93.0%

: 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

: 84066-39-7
(6E,10Z)-(3aR,4R,9S,11aS)-9-Benzyloxymethoxy-4-hydroxy-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Guidance literature:: With sodium tetrahydroborate; In methanol;
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

: 84066-39-7
(6E,10Z)-(3aR,4R,9S,11aS)-9-Benzyloxymethoxy-4-hydroxy-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Guidance literature:: Multi-step reaction with 6 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

6: 93 percent / NaBH₄ / methanol

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

: 84066-39-7
(6E,10Z)-(3aR,4R,9S,11aS)-9-Benzyloxymethoxy-4-hydroxy-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Guidance literature:: Multi-step reaction with 4 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

4: 93 percent / NaBH₄ / methanol

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