(3α,3aα,3bα,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopentapentalene

Base Information

• Chemical Name: (3α,3aα,3bα,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopenta
• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.409

Synonyms:

Chemical Property of (3α,3aα,3bα,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopenta

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

There total 27 articles about (3α,3aα,3bα,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopentapentalene 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:

6-<5-methoxy-3,3-dimethyl-2-tetrahydrofuranyl>fulvene (98330-87-1) → (3α,3aα,3bβ,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopentapentalene (110528-39-7,110611-19-3)

Guidance literature:

Multi-step reaction with 9 steps

1: diethyl ether / 2 h / 0 °C

2: dipotassium azodicarboxylate, acetic acid / CH₂Cl₂ / 3 h / 0 °C

3: 85 percent / 70percent aq. acetic acid / 120 h / 55 °C

4: 72.8 percent / LiClO₄ / dimethylformamide / electrolysis

5: 67 percent / methyl triphenylphosphonium bromide, n-BuLi / tetrahydrofuran; hexane / 3 h / Ambient temperature

6: methanol / 4 h / 61 °C

7: 93 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

8: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 2 h

9: 1.) pyridinium chlorochromate (PCC), celite, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1.) CH₂Cl₂, 0.5 h, 2.) CH₂Cl₂, RT, 2h

With pyridine; sodium hydroxide; n-butyllithium; borane-THF; Celite; dihydrogen peroxide; lithium perchlorate; Methyltriphenylphosphonium bromide; potassium diazodicarboxylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00230a001

Reference yield:

(3α,3aα,6aβ,7aα)-2,3,3a,5,6,6a,7,7a-octahydro-3-hydroxy-2,2-dimethyl-1H-cyclopentapentalene (98360-86-2,110611-12-6) → (3α,3aα,3bβ,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopentapentalene (110528-39-7,110611-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

2: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 2 h

3: 1.) pyridinium chlorochromate (PCC), celite, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1.) CH₂Cl₂, 0.5 h, 2.) CH₂Cl₂, RT, 2h

With pyridine; sodium hydroxide; borane-THF; Celite; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jo00230a001

Reference yield:

benzoyl chloride (98-88-4) → (3α,3aα,3bβ,6aβ,7aα)-decahydro-3-(benzyloxy)-2,2-dimethyl-4-oxo-1H-cyclopentapentalene (110528-39-7,110611-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

2: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 2 h

3: 1.) pyridinium chlorochromate (PCC), celite, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1.) CH₂Cl₂, 0.5 h, 2.) CH₂Cl₂, RT, 2h

With pyridine; sodium hydroxide; borane-THF; Celite; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jo00230a001

upstream raw materials:

Benzoic acid (3R,3aR,6aR,7aS)-4-hydroxy-2,2-dimethyl-decahydro-cyclopenta[a]pentalen-3-yl ester

benzoyl chloride

(3α,3aα,6aβ,7aα)-2,3,3a,5,6,6a,7,7a-octahydro-3-hydroxy-2,2-dimethyl-1H-cyclopentapentalene

6-<5-methoxy-3,3-dimethyl-2-tetrahydrofuranyl>fulvene

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