(3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one

Base Information

Chemical Name:(3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one
CAS No.:84066-34-2
Molecular Formula:C₂₄H₃₂O₅
Molecular Weight:400.515
Hs Code.:

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

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Chemical Property of (3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one

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Technology Process of (3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one

There total 1 articles about (3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-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:

: 84066-33-1
(1S,4S,6S)-4-Benzyloxymethoxy-1-(3,3-dimethoxy-cyclobut-1-enyl)-6-isopropenyl-3-methyl-cyclohex-2-enol

: 84107-75-5
(3Z,7E)-(1R,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one

: 84066-34-2
(3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one

Guidance literature:: With potassium hexamethylsilazane; In 1,2-dimethoxyethane; at 85 ℃; for 14h; Yield given. Yields of byproduct given;
DOI:10.1021/ja00341a055

Reference yield:

: 84066-34-2
(3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-11,11-dimethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-dien-2-one

: 38458-58-1
germacranolide eucannabinolide

Guidance literature:: Multi-step reaction with 16 steps

1: (COOH)2/silica gel / CH₂Cl₂ / 2 h / 35 °C

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

3: NaBH₄ / methanol / 0.5 h / 0 °C

4: 61 percent / K₂CO₃ / methanol / 5 h / 25 °C

5: 71 percent / Collins reagent / CH₂Cl₂ / 0.08 h / 25 °C

6: 70 percent / DBU / tetrahydrofuran / 3 h / 25 °C

7: 93 percent / NaBH₄ / methanol

8: 78 percent / H₂ / 20percent Pd(OH)2/C / aq. ethanol / 25 °C / 1137.7 Torr

9: C₅H₅N / CH₂Cl₂ / 25 °C

10: 1.) LDA / 1.) THF, 2.) -70 deg C

11: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 25 °C

12: DBU / dioxane / 0.5 h / 70 °C

13: Bu₄NF / tetrahydrofuran / 25 °C

14: 82 percent / DCC, 4-pyrrolidinopyridine

15: 52 percent / DCC, 4-pyrrolidinopyridine

16: 54 percent / C₅H₅NH⁺OTs^- / methanol; ethane-1,2-diol

With pyridine; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; Collins oxidation agent; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; oxalic acid; silica gel; potassium carbonate; 4-pyrrolidin-1-ylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethylene glycol;
DOI:10.1021/ja00341a055