(3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one

Base Information

• Chemical Name: (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one
• CAS No.: 71686-37-8
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435
• Mol file: 71686-37-8.mol

Synonyms:

Chemical Property of (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one

There total 25 articles about (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one 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:

benzyl bromide (100-39-0) → (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one (71686-37-8,73407-83-7,73407-85-9)

Guidance literature:

Multi-step reaction with 21 steps

1: 87 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 12 h

2: p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

3: 89 percent / 10percent aq. KOH / methanol / 21 h / 55 °C

4: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

5: 92 percent / DBU / toluene / 3 h / Heating

6: i-Bu₂AlH / toluene / 0.5 h / -78 °C

7: benzene / 1 h / Ambient temperature

8: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

9: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

10: 1.5percent KOH / methanol / 8 h / Ambient temperature

11: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

12: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

13: 96 percent / pyridine / 2 h / Ambient temperature

14: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

15: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

16: DBU / benzene / 0.25 h / Ambient temperature

17: LiAlH₄

18: MCPBA / CH₂Cl₂

19: Collins

20: 98 percent / NaBH₄ / ethanol / 1 h / 0 °C

21: 1.) diisopropylamine, n-BuLi, acetic acid / 1.) DME, hexane, -42 deg C, 10 min; 43 deg C, 90 min, 2.) 55 deg C, 20 h

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; jones reagent; Collins oxidation agent; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetone; toluene; benzene;

DOI:10.1021/ja00379a030

Reference yield:

(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone (68241-54-3) → (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one (71686-37-8,73407-83-7,73407-85-9)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄

2: MCPBA / CH₂Cl₂

3: Collins

4: 98 percent / NaBH₄ / ethanol / 1 h / 0 °C

5: 1.) diisopropylamine, n-BuLi, acetic acid / 1.) DME, hexane, -42 deg C, 10 min; 43 deg C, 90 min, 2.) 55 deg C, 20 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; acetic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane;

DOI:10.1021/ja00379a030

Reference yield:

(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol (71686-31-2) → (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one (71686-37-8,73407-83-7,73407-85-9)

Guidance literature:

Multi-step reaction with 15 steps

1: benzene / 1 h / Ambient temperature

2: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

3: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

4: 1.5percent KOH / methanol / 8 h / Ambient temperature

5: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

6: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

7: 96 percent / pyridine / 2 h / Ambient temperature

8: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

9: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

10: DBU / benzene / 0.25 h / Ambient temperature

11: LiAlH₄

12: MCPBA / CH₂Cl₂

13: Collins

14: 98 percent / NaBH₄ / ethanol / 1 h / 0 °C

15: 1.) diisopropylamine, n-BuLi, acetic acid / 1.) DME, hexane, -42 deg C, 10 min; 43 deg C, 90 min, 2.) 55 deg C, 20 h

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; jones reagent; Collins oxidation agent; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetone; benzene;

DOI:10.1021/ja00379a030

upstream raw materials:

(3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione

(3aα,4α,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one

(1aα,2β,4β,4aβ,7α,7aα,7bα)-1a,2,3,4,4a,7,7a,7b-Octahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2-ol

acetic acid

Downstream raw materials:

dl-Mexicanin I

dl-Linifolin A

(3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione

(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one