2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

Base Information

Chemical Name:2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one
CAS No.:81470-31-7
Molecular Formula:C₂₃H₃₀O₅Se
Molecular Weight:465.448
Hs Code.:

Synonyms:2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

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Chemical Property of 2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

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Technology Process of 2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

There total 12 articles about 2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-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:

: 51673-64-4
methyl 2-methyl-3-oxopropanoate

: 81470-31-7
2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 52 percent / KF / dimethylsulfoxide; 1,2-dimethoxy-ethane / 2 h

2: 96 percent / SOCl₂ / pyridine / 1 h

3: m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: 27 percent / pyridine; H₂O / 1.5 h / 35 - 37 °C

5: 1.) triphenylphosphine, acetic acid, diethyl azodicarboxylate, 2.) 6M HCl / 1.) THF, RT, 15h, 2.) dioxane, 20h, 30 deg C

6: 92 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

7: 1.) K₂CO₃, NaBH₄, 2.) HCl / 1.) methanol, water, DME, 1h, 2.) 0 deg C, 10 min

8: 100 percent / NaBH₄ / NiCl₂ hexahydrate / methanol / 2 h / 0 °C

9: 1.) LDA, 2.) HMPT / 1.) THF, -78 deg C to -20 deg C, 1,5h, 2.) -20 deg C to 0 deg C, 1,5h

10: 96 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

11: 1.) LDA, HMPT / 1.) THF, -78 deg C to -20 deg C, 1,5h, 2.) THF, -55 deg C to -30 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; potassium fluoride; nickel dichloride; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87730-9

Reference yield:

: 81470-12-4,117585-18-9,117585-19-0,117585-20-3
2,4,5,6,7,7aα-hexahydro-7β-hydroxy-6α-methoxycarbonyl-6β-methyl-3-phenylthio-1-benzofuran-2-one

: 81470-31-7
2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 96 percent / SOCl₂ / pyridine / 1 h

2: m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

3: 27 percent / pyridine; H₂O / 1.5 h / 35 - 37 °C

4: 1.) triphenylphosphine, acetic acid, diethyl azodicarboxylate, 2.) 6M HCl / 1.) THF, RT, 15h, 2.) dioxane, 20h, 30 deg C

5: 92 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

6: 1.) K₂CO₃, NaBH₄, 2.) HCl / 1.) methanol, water, DME, 1h, 2.) 0 deg C, 10 min

7: 100 percent / NaBH₄ / NiCl₂ hexahydrate / methanol / 2 h / 0 °C

8: 1.) LDA, 2.) HMPT / 1.) THF, -78 deg C to -20 deg C, 1,5h, 2.) -20 deg C to 0 deg C, 1,5h

9: 96 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) LDA, HMPT / 1.) THF, -78 deg C to -20 deg C, 1,5h, 2.) THF, -55 deg C to -30 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87730-9

Reference yield:

: 84607-44-3
2,4,5,6-tetrahydro-6-methoxycarbonyl-6-methyl-3-phenylthio-1-benzofuran-2-one

: 81470-31-7
2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3β-(4-methyl-3-pentenyl)-3-phenylselenenyl-1-benzofuran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

2: 27 percent / pyridine; H₂O / 1.5 h / 35 - 37 °C

3: 1.) triphenylphosphine, acetic acid, diethyl azodicarboxylate, 2.) 6M HCl / 1.) THF, RT, 15h, 2.) dioxane, 20h, 30 deg C

4: 92 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

5: 1.) K₂CO₃, NaBH₄, 2.) HCl / 1.) methanol, water, DME, 1h, 2.) 0 deg C, 10 min

6: 100 percent / NaBH₄ / NiCl₂ hexahydrate / methanol / 2 h / 0 °C

7: 1.) LDA, 2.) HMPT / 1.) THF, -78 deg C to -20 deg C, 1,5h, 2.) -20 deg C to 0 deg C, 1,5h

8: 96 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

9: 1.) LDA, HMPT / 1.) THF, -78 deg C to -20 deg C, 1,5h, 2.) THF, -55 deg C to -30 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87730-9