(3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

Base Information

Chemical Name:(3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid
CAS No.:84607-45-4
Molecular Formula:C₂₂H₂₈O₅Se
Molecular Weight:451.421
Hs Code.:

Synonyms:(3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

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Chemical Property of (3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

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Technology Process of (3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

There total 11 articles about (3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid 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:

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

: 84607-45-4
(3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

Guidance literature:: Multi-step reaction with 10 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

10: 1.) 10percent KOH, 2.) HCl / 1.) ethanol, 3h, reflux, 2.) 0 deg C, 30 min

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; 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

Reference yield:

: 82891-33-6
3-Benzenesulfinyl-6-methyl-2-oxo-2,4,5,6-tetrahydro-benzofuran-6-carboxylic acid methyl ester

: 84607-45-4
(3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 27 percent / pyridine; H₂O / 1.5 h / 35 - 37 °C

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

3: 92 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

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

5: 100 percent / NaBH₄ / NiCl₂ hexahydrate / methanol / 2 h / 0 °C

6: 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

7: 96 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

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

9: 1.) 10percent KOH, 2.) HCl / 1.) ethanol, 3h, reflux, 2.) 0 deg C, 30 min

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

Reference yield:

: 117585-21-4
2,4,5,6-tetrahydro-4β-t-butyldimethylsiloxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one

: 84607-45-4
(3S,3aR,4R,6R,7aS)-4-Hydroxy-6-methyl-3-(4-methyl-pent-3-enyl)-2-oxo-3-phenylselanyl-octahydro-benzofuran-6-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 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

4: 96 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

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

6: 1.) 10percent KOH, 2.) HCl / 1.) ethanol, 3h, reflux, 2.) 0 deg C, 30 min

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium carbonate; lithium diisopropyl amide; nickel dichloride; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4020(01)87730-9