Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-yl ester

Base Information

• Chemical Name: Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-yl ester
• CAS No.: 88764-02-7
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461

Synonyms:Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-yl ester

Chemical Property of Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-yl ester

There total 6 articles about Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-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: 43.0%

1β-Hydroxy-9β-benzoyloxy-2-keto-α-agarofuran (88703-21-3) → Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.01,6]dodec-2-en-7-yl ester (88764-02-7) + 1β,2β-Dihydroxy-9β-benzoyloxy-α-agarofuran (88703-23-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 25 ℃; for 3h;

DOI:10.1021/jo00180a006

Reference yield:

9β-hydroxy-α-agarofuran (85249-31-6,88764-01-6,85202-56-8) → Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.01,6]dodec-2-en-7-yl ester (88764-02-7)

Guidance literature:

Multi-step reaction with 5 steps

1: n-butyllithium, 2,2'-bipyridyl / 1. THF, hexane, 25 deg C, 10 min, 2. THF, reflux, 1h

2: 60 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 5 h / -20 °C

3: 1. LDA, 2,2'-bipyridyl, 2. HMPA / 1. THF, hexane, 0 deg C, 45 min, 2. THF, 25 deg C, 18h

4: 1. m-chloro-perbenzoic acid, 2. HCl / 1. hexane, ambient temp., 4h, 2. THF, 25 deg C, 20 h

5: 32 percent / NaBH₄ / CeCl₃*7H₂O / methanol / 3 h / 25 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; [2,2]bipyridinyl; sodium tetrahydroborate; n-butyllithium; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; cerium(III) chloride; In methanol; dichloromethane;

DOI:10.1021/jo00180a006

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (1R,4R,5R,6R,7R,9S)-4,5-dihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.01,6]dodec-2-en-7-yl ester (88764-02-7)

Guidance literature:

Multi-step reaction with 5 steps

1: n-butyllithium, 2,2'-bipyridyl / 1. THF, hexane, 25 deg C, 10 min, 2. THF, reflux, 1h

2: 60 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 5 h / -20 °C

3: 1. LDA, 2,2'-bipyridyl, 2. HMPA / 1. THF, hexane, 0 deg C, 45 min, 2. THF, 25 deg C, 18h

4: 1. m-chloro-perbenzoic acid, 2. HCl / 1. hexane, ambient temp., 4h, 2. THF, 25 deg C, 20 h

5: 32 percent / NaBH₄ / CeCl₃*7H₂O / methanol / 3 h / 25 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; [2,2]bipyridinyl; sodium tetrahydroborate; n-butyllithium; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; cerium(III) chloride; In methanol; dichloromethane;

DOI:10.1021/jo00180a006

upstream raw materials:

1β-Hydroxy-9β-benzoyloxy-2-keto-α-agarofuran

9β-hydroxy-α-agarofuran

benzoyl chloride

9β-Benzoyloxy-α-agarofuran

Downstream raw materials:

1α-Hydroxy-2α-acetoxy-9β-benzoyloxy-α-agarofuran

2α-Acetoxy-2-keto-9β-benzoyloxy-α-agarofuran

2α-Acetoxy-1β-hydroxy-9β-benzoyloxy-α-agarofuran

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