(8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done

Base Information

• Chemical Name: (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done
• CAS No.: 350246-39-8
• Molecular Formula: C₂₇H₃₉NO₄
• Molecular Weight: 441.611
• Mol file: 350246-39-8.mol

Synonyms:(8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done

Chemical Property of (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done

There total 21 articles about (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done 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:

(8R,8aS)-6-((E)-(2R,6S)-6-Benzyloxymethoxy-1-hydroxy-2,5-dimethyl-oct-4-enyl)-8-hydroxy-8-methyl-hexahydro-indolizin-7-one (350246-38-7) → (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done (350246-39-8)

Guidance literature:

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; In dichloromethane; at -50 - 0 ℃; for 1.5h;

DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Reference yield:

2-bromopentan-3-one (815-52-1) → (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done (350246-39-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 47 percent / benzene

2.1: 83 percent / aq. NaOH

3.1: 85 percent / toluene / 6 h / 90 °C

4.1: 73 percent / catecholborane / (R)-CBS catalyst / toluene; CH₂Cl₂ / 24 h / -40 °C

5.1: 97 percent / Huenigs base; Bu₄NI / toluene / 14 h / Heating

6.1: 90 percent / TBAF / tetrahydrofuran / 2 h

7.1: 94 percent / NMO; TPAP / CH₂Cl₂ / 0.5 h

8.1: fluorene; KHDMS / tetrahydrofuran; hexamethylphosphoric acid triamide; toluene / 0.25 h / 0 °C

8.2: tetrahydrofuran; hexamethylphosphoric acid triamide; toluene / 0.25 h

9.1: 57 mg / DMAP; DBU; TFAA / CH₂Cl₂ / 1.5 h / -50 - 0 °C

With dmap; sodium hydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 9H-fluorene; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; benzo[1,3,2]dioxaborole; (R)-CBS catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; benzene; 3.1: Wittig olefination;

DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Reference yield:

triphenyl-(1-propionylethylidene)phosphorane (111114-35-3) → (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done (350246-39-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / toluene / 6 h / 90 °C

2.1: 73 percent / catecholborane / (R)-CBS catalyst / toluene; CH₂Cl₂ / 24 h / -40 °C

3.1: 97 percent / Huenigs base; Bu₄NI / toluene / 14 h / Heating

4.1: 90 percent / TBAF / tetrahydrofuran / 2 h

5.1: 94 percent / NMO; TPAP / CH₂Cl₂ / 0.5 h

6.1: fluorene; KHDMS / tetrahydrofuran; hexamethylphosphoric acid triamide; toluene / 0.25 h / 0 °C

6.2: tetrahydrofuran; hexamethylphosphoric acid triamide; toluene / 0.25 h

7.1: 57 mg / DMAP; DBU; TFAA / CH₂Cl₂ / 1.5 h / -50 - 0 °C

With dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 9H-fluorene; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; benzo[1,3,2]dioxaborole; (R)-CBS catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; 1.1: Wittig olefination;

DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

upstream raw materials:

(8R,8aS)-6-((E)-(2R,6S)-6-Benzyloxymethoxy-1-hydroxy-2,5-dimethyl-oct-4-enyl)-8-hydroxy-8-methyl-hexahydro-indolizin-7-one

2-bromopentan-3-one

triphenyl-(1-propionylethylidene)phosphorane

triphenyl(1-propionylethyl)phosphonium bromide

Downstream raw materials:

(7S,8R,8aS,6E)-7,8-Dihydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizidine