Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-yl ester

Base Information

• Chemical Name: Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-yl ester
• CAS No.: 114250-72-5
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445

Synonyms:Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-yl ester

Chemical Property of Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-yl ester

There total 8 articles about Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-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: 85.0%

benzoic acid anhydride (93-97-0) + (1R,5S,6S,7S,8R)-5,8-Dihydroxy-2,2,6,8-tetramethyl-11-oxa-tricyclo[5.3.2.01,6]dodec-9-en-12-one (114273-21-1) → Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.01,6]dodec-9-en-5-yl ester (114250-72-5)

Guidance literature:

With dmap; In 1,2-dichloro-ethane; at 50 ℃; for 2h;

DOI:10.1021/ja00219a059

Reference yield:

(3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one (14398-36-8) → Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.01,6]dodec-9-en-5-yl ester (114250-72-5)

Guidance literature:

Multi-step reaction with 8 steps

2: Wittig methylenation

3: 72 percent / CHCl₃ / 30 h / 23 °C

4: BF₃*Et₂O / -35 deg C, 1 h, 0 deg C, 15 min

5: DBN / 0.75 h / 23 °C

6: O₂ / 0.1percent methylene blue / CHCl₃ / 144 h / 0 °C / Irradiation

7: 97 percent / AlHg / tetrahydrofuran; H₂O / 0.17 h / 23 °C

8: 85 percent / DMAP / 1,2-dichloro-ethane / 2 h / 50 °C

With dmap; aluminium amalgam; 2,6-dichloro-benzonitrile; boron trifluoride diethyl etherate; oxygen; methylene blue; In tetrahydrofuran; chloroform; water; 1,2-dichloro-ethane;

DOI:10.1021/ja00219a059

Reference yield:

2,4,4-trimethyl-3-formyl-2-cyclohexen-1-ol (60078-92-4,14393-38-5) → Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.01,6]dodec-9-en-5-yl ester (114250-72-5)

Guidance literature:

Multi-step reaction with 7 steps

1: Wittig methylenation

2: 72 percent / CHCl₃ / 30 h / 23 °C

3: BF₃*Et₂O / -35 deg C, 1 h, 0 deg C, 15 min

4: DBN / 0.75 h / 23 °C

5: O₂ / 0.1percent methylene blue / CHCl₃ / 144 h / 0 °C / Irradiation

6: 97 percent / AlHg / tetrahydrofuran; H₂O / 0.17 h / 23 °C

7: 85 percent / DMAP / 1,2-dichloro-ethane / 2 h / 50 °C

With dmap; aluminium amalgam; 2,6-dichloro-benzonitrile; boron trifluoride diethyl etherate; oxygen; methylene blue; In tetrahydrofuran; chloroform; water; 1,2-dichloro-ethane;

DOI:10.1021/ja00219a059

upstream raw materials:

benzoic acid anhydride

(1R,5S,6S,7S,8R)-5,8-Dihydroxy-2,2,6,8-tetramethyl-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-12-one

2,4,4-trimethyl-3-formyl-2-cyclohexen-1-ol

(3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one

Downstream raw materials:

(1S,4aR,8R,8aR)-8-Benzoyloxy-2,5,5,8a-tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid

(1S,4aR,8R,8aR)-8-Benzoyloxy-2,5,5,8a-tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

C₃₀H₃₉NO₉Se

(+/-)-desacetyl forskolin

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