(7aS,8S)-5,6,7,7a,8,9-Hexahydro-6,6,8-trimethylazuleno[5,6-c]furan-8-ol

Base Information

• Chemical Name: (7aS,8S)-5,6,7,7a,8,9-Hexahydro-6,6,8-trimethylazuleno[5,6-c]furan-8-ol
• CAS No.: 72601-37-7
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 72601-37-7.mol

Synonyms:

Chemical Property of (7aS,8S)-5,6,7,7a,8,9-Hexahydro-6,6,8-trimethylazuleno[5,6-c]furan-8-ol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7aS,8S)-5,6,7,7a,8,9-Hexahydro-6,6,8-trimethylazuleno[5,6-c]furan-8-ol

There total 34 articles about (7aS,8S)-5,6,7,7a,8,9-Hexahydro-6,6,8-trimethylazuleno[5,6-c]furan-8-ol 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:

dimedone (126-81-8) → epi-Furoscrobiculin B (72601-37-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 1) aq. NaHCO₃, 2) aq. H₂SO₄ / 1) CHCl₃, r.t., 2) r.t.

2: 94 percent / NaBH₄ / ethanol / Ambient temperature

3: 99 percent / NaH / dimethylformamide / Ambient temperature

4: 95 percent / POCl₃ / Ambient temperature

5: NaBH₄ / ethanol / Ambient temperature

6: 98 percent / aq. NaOH / Bu₄NHSO₄ / diethyl ether / Ambient temperature

7: tBuOK / 2-methyl-propan-2-ol / 70 °C

8: Li / liquid ammonia; tetrahydrofuran / -78 °C

9: 46 percent / PDC / CH₂Cl₂ / Ambient temperature

10: 85 percent / DIBAH / tetrahydrofuran / -78 °C

11: 33 percent / OsO₄ / CH₂Cl₂; pyridine / Ambient temperature

12: 80 percent / DMAP, NEt₃ / CH₂Cl₂ / 40 °C

13: 97 percent / tBuOK / 2-methyl-propan-2-ol / Ambient temperature

14: Al₂O₃ / pyridine / 110 °C

15: 79 percent / CeCl₃ / tetrahydrofuran / -78 °C

16: tBuOK / dimethylformamide / Ambient temperature

With dmap; aluminum oxide; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; cerium(III) chloride; sulfuric acid; potassium tert-butylate; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; trichlorophosphate; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; ammonia; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39940001979

Reference yield:

dimedone (126-81-8) → Furoscrobiculin B (72601-37-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 1) aq. NaHCO₃, 2) aq. H₂SO₄ / 1) CHCl₃, r.t., 2) r.t.

2: 94 percent / NaBH₄ / ethanol / Ambient temperature

3: 99 percent / NaH / dimethylformamide / Ambient temperature

4: 95 percent / POCl₃ / Ambient temperature

5: NaBH₄ / ethanol / Ambient temperature

6: 98 percent / aq. NaOH / Bu₄NHSO₄ / diethyl ether / Ambient temperature

7: tBuOK / 2-methyl-propan-2-ol / 70 °C

8: Li / liquid ammonia; tetrahydrofuran / -78 °C

9: 46 percent / PDC / CH₂Cl₂ / Ambient temperature

10: 85 percent / DIBAH / tetrahydrofuran / -78 °C

11: 33 percent / OsO₄ / CH₂Cl₂; pyridine / Ambient temperature

12: 80 percent / DMAP, NEt₃ / CH₂Cl₂ / 40 °C

13: 97 percent / tBuOK / 2-methyl-propan-2-ol / Ambient temperature

14: Al₂O₃ / pyridine / 110 °C

15: 79 percent / CeCl₃ / tetrahydrofuran / -78 °C

16: tBuOK / dimethylformamide / Ambient temperature

With dmap; aluminum oxide; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; cerium(III) chloride; sulfuric acid; potassium tert-butylate; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; trichlorophosphate; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; ammonia; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39940001979

Reference yield:

4-oxo-6,6-dimethyl-4,5,6,7-tetrahydrobenzofuran (76230-27-8) → epi-Furoscrobiculin B (72601-37-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 94 percent / NaBH₄ / ethanol / Ambient temperature

2: 99 percent / NaH / dimethylformamide / Ambient temperature

3: 95 percent / POCl₃ / Ambient temperature

4: NaBH₄ / ethanol / Ambient temperature

5: 98 percent / aq. NaOH / Bu₄NHSO₄ / diethyl ether / Ambient temperature

6: tBuOK / 2-methyl-propan-2-ol / 70 °C

7: Li / liquid ammonia; tetrahydrofuran / -78 °C

8: 46 percent / PDC / CH₂Cl₂ / Ambient temperature

9: 85 percent / DIBAH / tetrahydrofuran / -78 °C

10: 33 percent / OsO₄ / CH₂Cl₂; pyridine / Ambient temperature

11: 80 percent / DMAP, NEt₃ / CH₂Cl₂ / 40 °C

12: 97 percent / tBuOK / 2-methyl-propan-2-ol / Ambient temperature

13: Al₂O₃ / pyridine / 110 °C

14: 79 percent / CeCl₃ / tetrahydrofuran / -78 °C

15: tBuOK / dimethylformamide / Ambient temperature

With dmap; aluminum oxide; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; cerium(III) chloride; potassium tert-butylate; lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; trichlorophosphate; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; ammonia; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39940001979

upstream raw materials:

4,5,6,7,8,9-Hexahydro-6,6,8-trimethylazuleno<5,6-c>furan-8-ol

dimedone

4-oxo-6,6-dimethyl-4,5,6,7-tetrahydrobenzofuran

6,6-dimethyl-4-hydroxytetrahydrobenzofuran

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