(1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one

Base Information

• Chemical Name: (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one
• CAS No.: 162599-60-2
• Molecular Formula: C₂₇H₄₀O₄SeSi
• Molecular Weight: 535.658
• Mol file: 162599-60-2.mol

Synonyms:

Chemical Property of (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one

There total 32 articles about (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-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:

(3aS,7aS)-6-methyl-3,3a,7,7a-tetrahydrobenzofuran-2,4-dione (162460-69-7) → (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one (162599-60-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CeCl₃*7H₂O, NaBH₄, 2.) NaHCO₃, mCPBA / 1) methanol, 0 deg C, 1.5 h; 2) CH₂Cl₂, 0 deg C, 3.5 h, 5 deg C, 12 h

2: 75 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

3: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 20 min, -40 deg C, 1 h; 2) THF, -78 deg C, 20 min, 5 deg C, 15 h

4: 1.) potassium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 5 min; 2) THF, HMPA, -78 deg C, 1 h

With dmap; sodium tetrahydroborate; cerium(III) chloride; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1016/S0040-4020(99)00096-4

Reference yield:

(3aR,4S,5S,6R.7aS)-5,6-epoxy-3a,4,5,6,7,7a-hexahydro-4-hydroxy-6-methyl-2(3H)-benzofuranone (162599-57-7) → (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one (162599-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 20 min, -40 deg C, 1 h; 2) THF, -78 deg C, 20 min, 5 deg C, 15 h

3: 1.) potassium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 5 min; 2) THF, HMPA, -78 deg C, 1 h

With dmap; potassium hexamethylsilazane; triethylamine; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1016/S0040-4020(99)00096-4

Reference yield:

(3aS,7aS)-3,3a,7,7a-tetrahydrobenzofuran-2,4-dione (226885-84-3) → (1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one (162599-60-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) CuI, 3.) Et₃N / 1) diethyl ether, THF, -78 deg C, 1 h; 2) THF, diethyl ether, -78 deg C, 1 h; 3) THF, diethyl ether, -78 deg C, 10 min, 0 deg C, 2 h

2: Pd(AAc)2 / acetonitrile / 72 h / Ambient temperature

3: 1.) CeCl₃*7H₂O, NaBH₄, 2.) NaHCO₃, mCPBA / 1) methanol, 0 deg C, 1.5 h; 2) CH₂Cl₂, 0 deg C, 3.5 h, 5 deg C, 12 h

4: 75 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

5: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 20 min, -40 deg C, 1 h; 2) THF, -78 deg C, 20 min, 5 deg C, 15 h

6: 1.) potassium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 5 min; 2) THF, HMPA, -78 deg C, 1 h

With dmap; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; Pd(AAc)2; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(99)00096-4

upstream raw materials:

diphenyl diselenide

(1aS,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one

5-iodo-2-methylpent-2-ene

(3aS,7aS)-6-methyl-3,3a,7,7a-tetrahydrobenzofuran-2,4-dione

Downstream raw materials:

(+)-paniculide A