4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

Base Information

Chemical Name:4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester
CAS No.:325142-48-1
Molecular Formula:C₂₇H₂₉NO₅
Molecular Weight:447.531
Hs Code.:

Synonyms:4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

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Chemical Property of 4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

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Technology Process of 4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

There total 12 articles about 4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester 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:

: 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

: 62-23-7
4-nitro-benzoic acid

: 325142-48-1
4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20 ℃;
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

: 325142-48-1
4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

Guidance literature:: Multi-step reaction with 13 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

With 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; 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:

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

: 325142-48-1
4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester

Guidance literature:: Multi-step reaction with 12 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

With 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; diphenylether; ethanol; dichloromethane; 2: Eschenmoser rearrangement / 4: Pauson-Khand reaction / 10: retro-Diels-Alder reaction / 11: Wolff-Kishner reaction;
DOI:10.1021/ol006922o