(3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

Base Information

Chemical Name:(3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one
CAS No.:76461-61-5
Molecular Formula:C₂₆H₃₄O₃Se
Molecular Weight:473.514
Hs Code.:

(3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

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Chemical Property of (3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

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Technology Process of (3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

There total 19 articles about (3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-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:

: 68317-62-4,10095-77-9,41164-15-2,68366-26-7,71048-52-7,72059-04-2,92334-78-6
bicyclo[3.3.0]oct-7-en-endo-2-ol

: 76461-61-5
(3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) sodium hydride / 1.) DMF, 0 deg C (adding), then RT, 45 min, 2.) DMF, 50-60 deg C, 1 h

2: N-bromosuccinimide / dimethylsulfoxide; H₂O / 0 deg C, 5 min, then RT, 0.5 h

3: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

4: PCC / CH₂Cl₂ / 3.5 h / Ambient temperature

5: imidazol / dimethylformamide / 0 deg C, 0.5 h, then RT, 1.5 h

6: DBU / benzene / 0.08 h / Ambient temperature

7: 95 percent / diethyl ether / - 78 deg C, 15 min, then without cooling, 10 min

8: 77 percent / potassium t-butoxide / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) up to 0 deg C, then 0 deg C, 10 min

9: lithium wire / liquid ammonia; tetrahydrofuran / 4 h

10: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

11: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

12: 94 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 6 h / Ambient temperature

13: NaH / 1.) DME, 0 deg C (adding), then RT, 2 h, 2.) 0 deg C (adding), then RT, 1.5 h

14: 1.) O₂, CuCl, PdCl₂, 2.) O₂, 3.) p-toluenesulfonic acid / 1.) DMF-H₂O, RT, 2 h, 2.) RT, 24 h, 3.) CH₂Cl₂, 0 deg C, 20 min

15: 83 percent / potassium t-butoxide / 2-methyl-propan-2-ol / 0.17 h / 35 °C

16: 1.) diisopropylamine, n-BuLi / 1.) THF, -78 deg C, 10 min, then without cooling, 10 min, 2.) THF, -78 deg C, 10 min, 3.) up to RT, 30 min

17: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h, then up to RT, 60 min

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; oxygen; sodium acetate; lithium; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; pyridinium chlorochromate; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(81)80007-5

Reference yield:

: 76453-15-1,82653-87-0
(1S,2S,3aR,6R,6aS)-6-Benzyloxy-1-bromo-octahydro-pentalen-2-ol

: 76461-61-5
(3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

Guidance literature:: Multi-step reaction with 15 steps

1: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

2: PCC / CH₂Cl₂ / 3.5 h / Ambient temperature

3: imidazol / dimethylformamide / 0 deg C, 0.5 h, then RT, 1.5 h

4: DBU / benzene / 0.08 h / Ambient temperature

5: 95 percent / diethyl ether / - 78 deg C, 15 min, then without cooling, 10 min

6: 77 percent / potassium t-butoxide / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) up to 0 deg C, then 0 deg C, 10 min

7: lithium wire / liquid ammonia; tetrahydrofuran / 4 h

8: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

9: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

10: 94 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 6 h / Ambient temperature

11: NaH / 1.) DME, 0 deg C (adding), then RT, 2 h, 2.) 0 deg C (adding), then RT, 1.5 h

12: 1.) O₂, CuCl, PdCl₂, 2.) O₂, 3.) p-toluenesulfonic acid / 1.) DMF-H₂O, RT, 2 h, 2.) RT, 24 h, 3.) CH₂Cl₂, 0 deg C, 20 min

13: 83 percent / potassium t-butoxide / 2-methyl-propan-2-ol / 0.17 h / 35 °C

14: 1.) diisopropylamine, n-BuLi / 1.) THF, -78 deg C, 10 min, then without cooling, 10 min, 2.) THF, -78 deg C, 10 min, 3.) up to RT, 30 min

15: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h, then up to RT, 60 min

With 1H-imidazole; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; oxygen; sodium acetate; lithium; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; pyridinium chlorochromate; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(81)80007-5

Reference yield:

: 76453-14-0,82653-86-9,108391-94-2
(1RS,5RS,8RS)-8-benzyloxybicyclo<3.3.0>oct-2-ene

: 76461-61-5
(3aR,3bS,4S,6aR)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

Guidance literature:: Multi-step reaction with 16 steps

1: N-bromosuccinimide / dimethylsulfoxide; H₂O / 0 deg C, 5 min, then RT, 0.5 h

2: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

3: PCC / CH₂Cl₂ / 3.5 h / Ambient temperature

4: imidazol / dimethylformamide / 0 deg C, 0.5 h, then RT, 1.5 h

5: DBU / benzene / 0.08 h / Ambient temperature

6: 95 percent / diethyl ether / - 78 deg C, 15 min, then without cooling, 10 min

7: 77 percent / potassium t-butoxide / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) up to 0 deg C, then 0 deg C, 10 min

8: lithium wire / liquid ammonia; tetrahydrofuran / 4 h

9: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

10: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

11: 94 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 6 h / Ambient temperature

12: NaH / 1.) DME, 0 deg C (adding), then RT, 2 h, 2.) 0 deg C (adding), then RT, 1.5 h

13: 1.) O₂, CuCl, PdCl₂, 2.) O₂, 3.) p-toluenesulfonic acid / 1.) DMF-H₂O, RT, 2 h, 2.) RT, 24 h, 3.) CH₂Cl₂, 0 deg C, 20 min

14: 83 percent / potassium t-butoxide / 2-methyl-propan-2-ol / 0.17 h / 35 °C

15: 1.) diisopropylamine, n-BuLi / 1.) THF, -78 deg C, 10 min, then without cooling, 10 min, 2.) THF, -78 deg C, 10 min, 3.) up to RT, 30 min

16: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h, then up to RT, 60 min

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; oxygen; sodium acetate; lithium; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; pyridinium chlorochromate; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(81)80007-5