(1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

Base Information

Chemical Name:(1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol
CAS No.:325142-47-0
Molecular Formula:C₂₀H₂₆O₂
Molecular Weight:298.425
Hs Code.:

Synonyms:(1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

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Chemical Property of (1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

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Technology Process of (1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

There total 10 articles about (1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol 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:

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

: 325142-47-0
(1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

Guidance literature:: Multi-step reaction with 11 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

With N-Bromosuccinimide; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dimethyl sulfoxide; zinc; lithium diisopropyl amide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; In tetrahydrofuran; 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

: 325142-47-0
(1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

Guidance literature:: Multi-step reaction with 12 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

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

Reference yield:

: 325142-37-8
C₁₁H₁₃BrO₂

: 325142-47-0
(1R,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-1,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / diphenyl ether / Heating

2: 75 percent / LDA / tetrahydrofuran / -78 °C

3: 66 percent / DMSO / CH₂Cl₂ / Heating

4: 94 percent / tetrahydrofuran / -20 °C

5: p-TsOH

6: 90 percent / Li(Et)3BH / tetrahydrofuran

7: 87 percent / NaH / tetrahydrofuran

8: 85 percent / Zn; acetic acid / ethanol / Heating

9: 91 percent / NaHCO₃ / diphenyl ether / Heating

10: 93 percent / NH₂NH₂*H₂O; K₂CO₃; TEG / 250 °C

With sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dimethyl sulfoxide; zinc; lithium diisopropyl amide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; In tetrahydrofuran; diphenylether; ethanol; dichloromethane; 1: Eschenmoser rearrangement / 3: Pauson-Khand reaction / 9: retro-Diels-Alder reaction / 10: Wolff-Kishner reaction;
DOI:10.1021/ol006922o