Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-4-en-7-yl ester

Base Information

• Chemical Name: Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-4-en-7-yl ester
• CAS No.: 102342-24-5
• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.462

Synonyms:Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-4-en-7-yl ester

Chemical Property of Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-4-en-7-yl ester

Chemical Property:

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Technology Process of Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-4-en-7-yl ester

There total 17 articles about Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-4-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: 87.0%

2α-selenophenyl-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran (117212-75-6) → 1,2-dehydro-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran (102342-24-5)

Guidance literature:

With diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(01)87737-1

Reference yield:

9-keto-α-agarofuran (85249-30-5) → Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.01,6]dodec-4-en-7-yl ester (102342-24-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) MCPA, aq. NaHCO₃, 2.) LDA / 1.) CH₂Cl₂, 25 deg C, 6 h, 2.) ether, 25 deg C, 6 h

2: 90 percent / NH₂NH₂, NaIO₄, CuSO₄ / acetic acid; ethanol / 6 h / 25 °C

3: 65 percent / POCl₃, pyridine / 1 h / Heating

4: LiAlH₄ / diethyl ether / 1.) -50 deg C, 5 h, 2.) 25 deg C, 18 h

5: 1.) BuLi / 1.) THF, 25 deg C, 10 min, 2.) THF, a.) 25 deg C, 15 min, b.) 65 deg C, 1 h

6: 60 percent / MCPA / CH₂Cl₂ / 17 h / 25 °C

7: 1.) (PhSe)2, NaBH₄, 2.) MCPA, (i-P)2rNH / 1.) EtOH, reflux, 2 h, 2.) CH₂Cl₂, -78 deg C, 1 h

With pyridine; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; diphenyl diselenide; MCPA; sodium hydrogencarbonate; copper(II) sulfate; diisopropylamine; hydrazine; lithium diisopropyl amide; trichlorophosphate; In diethyl ether; ethanol; dichloromethane; acetic acid;

DOI:10.1021/jo00361a049

Reference yield:

(1S,2R,6S,7S,9R)-2,6,10,10-Tetramethyl-11-oxa-tricyclo[7.2.1.01,6]dodec-3-en-7-ol (117212-74-5) → Benzoic acid (1R,2S,3R,6R,7R,9S)-3-hydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.01,6]dodec-4-en-7-yl ester (102342-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) THF, 25 deg C, 10 min, 2.) THF, a.) 25 deg C, 15 min, b.) 65 deg C, 1 h

2: 60 percent / MCPA / CH₂Cl₂ / 17 h / 25 °C

3: 1.) (PhSe)2, NaBH₄, 2.) MCPA, (i-P)2rNH / 1.) EtOH, reflux, 2 h, 2.) CH₂Cl₂, -78 deg C, 1 h

With sodium tetrahydroborate; n-butyllithium; diphenyl diselenide; MCPA; diisopropylamine; In dichloromethane;

DOI:10.1021/jo00361a049

upstream raw materials:

2α-selenophenyl-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

benzoyl chloride

2,3-dehydro-4α-methyl-9β-hydroxydihydroagarofuran

2,3-dehydro-4α-methyl-9-ketodihydroagarofuran

Downstream raw materials:

1α,2α,3β-trihydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

Benzoic acid (1S,2R,3R,4S,5R,6S,7S,9R)-3,4,5-trihydroxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-7-yl ester

C₂₅H₃₄O₅

(+/-)-isocelorbicol

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