Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Base Information

Chemical Name:Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester
CAS No.:110528-28-4
Molecular Formula:C₂₄H₃₄O₃Si
Molecular Weight:398.618
Hs Code.:

Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

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Chemical Property of Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

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Technology Process of Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

There total 14 articles about Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]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:

: 98330-87-1
6-<5-methoxy-3,3-dimethyl-2-tetrahydrofuranyl>fulvene

: 110528-28-4
Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Guidance literature:: Multi-step reaction with 11 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: 2.) 3-chloroperbenzoic acid, Na₂CO₃ / 1.) MeOH, 61 deg C, 4 h, 2.) CHCl₃, 0 deg C, 10 min

7: lithium diisopropylamide (LDA) / tetrahydrofuran / 4 h / Heating

8: 89 percent / pyridine / CH₂Cl₂ / 11 h / Ambient temperature

9: 85 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 6 h / Ambient temperature

10: 1.) CuCN, 2.) BF₃*OEt₂ / 2.) THF, -50 - -55 deg C, 3 h

11: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to 0 deg C

With pyridine; n-butyllithium; Celite; boron trifluoride diethyl etherate; lithium perchlorate; Methyltriphenylphosphonium bromide; potassium diazodicarboxylate; sodium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00230a001

Reference yield:

: 110528-23-9,110611-13-7
(3aS,4aR,7S,7aR)-6,6-Dimethyl-decahydro-1-oxa-cyclopenta[a]cyclopropa[g]pentalen-7-ol

: 110528-28-4
Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: lithium diisopropylamide (LDA) / tetrahydrofuran / 4 h / Heating

2: 89 percent / pyridine / CH₂Cl₂ / 11 h / Ambient temperature

3: 85 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 6 h / Ambient temperature

4: 1.) CuCN, 2.) BF₃*OEt₂ / 2.) THF, -50 - -55 deg C, 3 h

5: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to 0 deg C

With pyridine; Celite; boron trifluoride diethyl etherate; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00230a001

Reference yield:

: 98330-89-3,110611-02-4,110611-03-5,110611-04-6,110611-05-7
N,N'-bis(methoxycarbonyl)-2,3-diaza-7-<5'-hydroxy-3,3-dimethyl-2-tetrahydrofuranylidene>bicyclo<2.2.1>heptane

: 110528-28-4
Benzoic acid (3R,3aR,3bR,6aS,7aS)-2,2,3b-trimethyl-5-trimethylsilanyloxy-2,3,3a,3b,4,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / KOH / ethanol / 1.5 h / Heating

2: 67 percent / methyl triphenylphosphonium bromide, n-BuLi / tetrahydrofuran; hexane / 3 h / Ambient temperature

3: 2.) 3-chloroperbenzoic acid, Na₂CO₃ / 1.) MeOH, 61 deg C, 4 h, 2.) CHCl₃, 0 deg C, 10 min

4: lithium diisopropylamide (LDA) / tetrahydrofuran / 4 h / Heating

5: 89 percent / pyridine / CH₂Cl₂ / 11 h / Ambient temperature

6: 85 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 6 h / Ambient temperature

7: 1.) CuCN, 2.) BF₃*OEt₂ / 2.) THF, -50 - -55 deg C, 3 h

8: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to 0 deg C

With pyridine; potassium hydroxide; n-butyllithium; Celite; boron trifluoride diethyl etherate; Methyltriphenylphosphonium bromide; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.1021/jo00230a001