(4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

Base Information

• Chemical Name: (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester
• CAS No.: 90127-21-2
• Molecular Formula: C₂₃H₂₄O₇
• Molecular Weight: 412.439

Synonyms:

Chemical Property of (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

There total 22 articles about (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-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:

benzoyl chloride (98-88-4) → (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester (90127-21-2)

Guidance literature:

Multi-step reaction with 14 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

13: 84 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

14: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, a.) -15 deg C, 30 min; b.) RT, 2 h; 2.) t-BuOH-H₂O, RT, 4 h

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium periodate; N-Bromosuccinimide; formic acid; selenium(IV) oxide; jones reagent; sodium cyanide; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; diborane; In tetrahydrofuran; ethanol; acetic acid; benzene;

DOI:10.1246/cl.1984.1923

Reference yield:

(Z)-(1R,3aS,4S,9aS)-4-Methoxy-2,2,4,8-tetramethyl-2,3,3a,4,5,6,9,9a-octahydro-1H-cyclopentacycloocten-1-ol (90144-72-2) → (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester (90127-21-2)

Guidance literature:

Multi-step reaction with 14 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

13: 84 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

14: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, a.) -15 deg C, 30 min; b.) RT, 2 h; 2.) t-BuOH-H₂O, RT, 4 h

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium periodate; N-Bromosuccinimide; formic acid; selenium(IV) oxide; jones reagent; sodium cyanide; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; diborane; In tetrahydrofuran; ethanol; acetic acid; benzene;

DOI:10.1246/cl.1984.1923

Reference yield:

((Z)-(1R,3aS,4S,9aS)-4-Methoxy-2,2,4,8-tetramethyl-2,3,3a,4,5,6,9,9a-octahydro-1H-cyclopentacycloocten-1-yloxy)-trimethyl-silane → (4aR,6aS,7R,9aR)-7-Benzoyloxy-4-hydroxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester (90127-21-2)

Guidance literature:

Multi-step reaction with 15 steps

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

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

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

4: Jones reagent / 0 °C

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

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

7: 37 percent / 48 h / 85 °C

8: 79 percent / SeO₂ / ethanol / 48 h / Heating

9: 91 percent / MnO₂, NaCN / acetic acid / 24 h / Ambient temperature

10: 78 percent / Jones reagent / 0 °C

11: Et₃N / benzene / 0.17 h / Ambient temperature

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

13: 33 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

14: 84 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

15: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, a.) -15 deg C, 30 min; b.) RT, 2 h; 2.) t-BuOH-H₂O, RT, 4 h

With pyridine; hydrogenchloride; manganese(IV) oxide; sodium hydroxide; sodium periodate; N-Bromosuccinimide; formic acid; selenium(IV) oxide; jones reagent; sodium cyanide; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; diborane; In tetrahydrofuran; methanol; diethyl ether; ethanol; acetic acid; benzene;

DOI:10.1246/cl.1984.1923

upstream raw materials:

(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

benzoyl chloride

(Z)-(1R,3aS,4S,9aS)-4-Methoxy-2,2,4,8-tetramethyl-2,3,3a,4,5,6,9,9a-octahydro-1H-cyclopentacycloocten-1-ol

Benzoic acid (3S,3aR,5R,5aS,8aR)-5a-hydroxy-2,2,5,8-tetramethyl-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalen-3-yl ester

Downstream raw materials:

(4aR,6aS,7R,9aS)-7-Benzoyloxy-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

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