(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester
CAS No.:94835-95-7
Molecular Formula:C₂₃H₂₄O₅
Molecular Weight:380.441
Hs Code.:

Synonyms:(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

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Chemical Property of (3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

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Technology Process of (3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

There total 22 articles about (3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl 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: 45.0%

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 90127-13-2
(1S,3aS,5aS,6R,8aS)-6-Benzoyloxy-1-bromo-1,7,7-trimethyl-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

: 94835-95-7
(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

: 90127-14-3
(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-trimethylsilanyloxy-1,3a,5a,6,7,8-hexahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

Guidance literature:: With sodium hydrogencarbonate; triethylamine; In benzene; for 24h; Ambient temperature;
DOI:10.1246/cl.1984.1923

Reference yield:

: 98-88-4
benzoyl chloride

: 94835-95-7
(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: pyridine / 1.) 0 deg C, 30 min; 2.) RT, 1 h

2: 1.) B₂H₆; 2.) H₂O₂, 3M NaOH / 1.) THF, 0 deg C, 30 min

3: Jones reagent / 0 °C

4: 1.) HCO₂H; 2.) Na₂CO₃ / 1.) 45 deg C, 36 h; 2.) MeOH-H₂O, RT, 5 h

5: 1.) B₂H₆; 2.) H₂O₂, NaOH / 1.) THF, a.) 0 deg C, 30 min; b.) RT, 1.5 h

6: 37 percent / 48 h / 85 °C

7: 79 percent / SeO₂ / ethanol / 48 h / Heating

8: 91 percent / MnO₂, NaCN / acetic acid / 24 h / Ambient temperature

9: 78 percent / Jones reagent / 0 °C

10: Et₃N / benzene / 0.17 h / Ambient temperature

11: NBS / tetrahydrofuran / 0.08 h / 0 °C

12: 33 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

With pyridine; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; formic acid; selenium(IV) oxide; jones reagent; sodium cyanide; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate; triethylamine; diborane; In tetrahydrofuran; ethanol; acetic acid; benzene;
DOI:10.1246/cl.1984.1923

Reference yield:

: 78098-01-8,78148-94-4
3,6-epxoy-3,6-seco-7⁽¹³⁾-protoilluden-10-ol

: 94835-95-7
(3aS,5aR,6S,8aR)-6-Benzoyloxy-7,7-dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: Et₃N / CH₂Cl₂ / 1.) 0 deg C, 15 min; 2.) RT, 1 h

2: Li/EtNH₂ / tetrahydrofuran / 3 h / -78 °C

3: NaH / tetrahydrofuran / 1 h / Heating

4: HCl / methanol; diethyl ether / 1 h / 0 °C

5: pyridine / 1.) 0 deg C, 30 min; 2.) RT, 1 h

6: 1.) B₂H₆; 2.) H₂O₂, 3M NaOH / 1.) THF, 0 deg C, 30 min

7: Jones reagent / 0 °C

8: 1.) HCO₂H; 2.) Na₂CO₃ / 1.) 45 deg C, 36 h; 2.) MeOH-H₂O, RT, 5 h

9: 1.) B₂H₆; 2.) H₂O₂, NaOH / 1.) THF, a.) 0 deg C, 30 min; b.) RT, 1.5 h

10: 37 percent / 48 h / 85 °C

11: 79 percent / SeO₂ / ethanol / 48 h / Heating

12: 91 percent / MnO₂, NaCN / acetic acid / 24 h / Ambient temperature

13: 78 percent / Jones reagent / 0 °C

14: Et₃N / benzene / 0.17 h / Ambient temperature

15: NBS / tetrahydrofuran / 0.08 h / 0 °C

16: 33 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

With pyridine; hydrogenchloride; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; formic acid; selenium(IV) oxide; jones reagent; sodium cyanide; dihydrogen peroxide; lithium; sodium hydride; sodium hydrogencarbonate; sodium carbonate; ethylamine; triethylamine; diborane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetic acid; benzene;
DOI:10.1246/cl.1984.1923