4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

Base Information

Chemical Name:4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one
CAS No.:325142-50-5
Molecular Formula:C₂₀H₂₄O₂
Molecular Weight:296.409
Hs Code.:

4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3a<i>H</i>-cyclopenta[<i>c</i>]pentalen-3-one

Synonyms:4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

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Chemical Property of 4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

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Technology Process of 4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

There total 14 articles about 4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-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: 81.0%

: 325142-49-2
(3S,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-ol

: 325142-50-5
4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

Guidance literature:: With manganese(IV) oxide; In dichloromethane; at 20 ℃;
DOI:10.1021/ol006922o

Reference yield:

: 244616-79-3
(1R,3aR,4R,7S,7aR)-2-Hydroxymethyl-3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-ol

: 325142-50-5
4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

Guidance literature:: Multi-step reaction with 14 steps

1: 99 percent / NBS / CH₂Cl₂ / 0 °C

2: 87 percent / diphenyl ether / Heating

3: 75 percent / LDA / tetrahydrofuran / -78 °C

4: 66 percent / DMSO / CH₂Cl₂ / Heating

5: 94 percent / tetrahydrofuran / -20 °C

6: p-TsOH

7: 90 percent / Li(Et)3BH / tetrahydrofuran

8: 87 percent / NaH / tetrahydrofuran

9: 85 percent / Zn; acetic acid / ethanol / Heating

10: 91 percent / NaHCO₃ / diphenyl ether / Heating

11: 93 percent / NH₂NH₂*H₂O; K₂CO₃; TEG / 250 °C

12: Ph₃P; DIAD / CH₂Cl₂ / 20 °C

13: aq. NaOH / methanol / 20 °C

14: 81 percent / MnO₂ / CH₂Cl₂ / 20 °C

With manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; di-isopropyl azodicarboxylate; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dimethyl sulfoxide; triphenylphosphine; zinc; lithium diisopropyl amide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; 2: Eschenmoser rearrangement / 4: Pauson-Khand reaction / 10: retro-Diels-Alder reaction / 11: Wolff-Kishner reaction;
DOI:10.1021/ol006922o

Reference yield:

: 325142-36-7
(3aR,4R,7S,7aR)-2-Hydroxymethyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one

: 325142-50-5
4-benzyloxymethyl-5a-methyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one

Guidance literature:: Multi-step reaction with 15 steps

1: DIBAL

2: 99 percent / NBS / CH₂Cl₂ / 0 °C

3: 87 percent / diphenyl ether / Heating

4: 75 percent / LDA / tetrahydrofuran / -78 °C

5: 66 percent / DMSO / CH₂Cl₂ / Heating

6: 94 percent / tetrahydrofuran / -20 °C

7: p-TsOH

8: 90 percent / Li(Et)3BH / tetrahydrofuran

9: 87 percent / NaH / tetrahydrofuran

10: 85 percent / Zn; acetic acid / ethanol / Heating

11: 91 percent / NaHCO₃ / diphenyl ether / Heating

12: 93 percent / NH₂NH₂*H₂O; K₂CO₃; TEG / 250 °C

13: Ph₃P; DIAD / CH₂Cl₂ / 20 °C

14: aq. NaOH / methanol / 20 °C

15: 81 percent / MnO₂ / CH₂Cl₂ / 20 °C

With manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; di-isopropyl azodicarboxylate; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dimethyl sulfoxide; triphenylphosphine; zinc; lithium diisopropyl amide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; 3: Eschenmoser rearrangement / 5: Pauson-Khand reaction / 11: retro-Diels-Alder reaction / 12: Wolff-Kishner reaction;
DOI:10.1021/ol006922o