3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione

Base Information

Chemical Name:3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione
CAS No.:84009-45-0
Molecular Formula:C₂₂H₃₂O₆S
Molecular Weight:424.558
Hs Code.:

Synonyms:

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Chemical Property of 3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione

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Technology Process of 3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione

There total 11 articles about 3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione 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: 80.0%

: 83999-40-0,84026-49-3
(Z)-3-Benzenesulfonyl-5-ethoxy-16-methyl-oxacyclohexadec-5-en-2-one

: 84009-45-0,84048-16-8
3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 16h; Product distribution; other base, other amount of oxidant;
DOI:10.1021/ja00341a043

Reference yield:

: 112-45-8
10-Undecenal

: 84009-45-0,84048-16-8
3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione

Guidance literature:: Multi-step reaction with 10 steps

1: 10.8 g / diethyl ether / reflux 10 min; RT, 10 min

2: 17.3 g / imidazole / dimethylformamide / 2 h / 35 °C

3: 1.) borane-methyl sulfide complex, 2-methyl-2-butene, 2.) 3N NaOH, 3.) 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) EtOH, 0 deg C -> RT, 3.) 25 deg C, then 55 deg C, 30 min

4: 93 percent / pyridinium chlorochromate / CH₂Cl₂ / 3.5 h / Heating

5: 1.) tert-BuLi / tetrahydrofuran; pentane / 1) -78 deg C, 10 min; 0 deg C, 5 min, 2.) -78 deg C -> RT

6: 8.33 g / pyridine / 15 h / 22 °C

7: 72 percent / tetrabutylammonium fluoride / tetrahydrofuran / 69 h / Ambient temperature

8: 69 percent / N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 41 h / Ambient temperature

9: 1.) O,N-bis(trimethylsilyl)acetamide, 2.) tetrakis(tetraphenylphosphine)palladium⁽⁰⁾, 1,3-bis(diphenylphosphino)propane / tetrahydrofuran / 16 h / Heating; other reagent, solvent, reaction time

10: 1.) OsO₄, 2.) NaHSO₃ / 1.) pyridine, 25 deg C, 5 h, 2.) pyridine-THF-H₂O, 10 min

With 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; 2-methyl-but-2-ene; dimethylsulfide borane complex; tetrakis(tetraphenylphosphine)palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; N,O-bis-(trimethylsilyl)-acetamide; sodium hydrogensulfite; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja00341a043

Reference yield:

: 21951-49-5
dodec-11-en-2-ol

: 84009-45-0,84048-16-8
3-Benzenesulfonyl-6-hydroxy-16-methyl-oxacyclohexadecane-2,5-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 17.3 g / imidazole / dimethylformamide / 2 h / 35 °C

2: 1.) borane-methyl sulfide complex, 2-methyl-2-butene, 2.) 3N NaOH, 3.) 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) EtOH, 0 deg C -> RT, 3.) 25 deg C, then 55 deg C, 30 min

3: 93 percent / pyridinium chlorochromate / CH₂Cl₂ / 3.5 h / Heating

4: 1.) tert-BuLi / tetrahydrofuran; pentane / 1) -78 deg C, 10 min; 0 deg C, 5 min, 2.) -78 deg C -> RT

5: 8.33 g / pyridine / 15 h / 22 °C

6: 72 percent / tetrabutylammonium fluoride / tetrahydrofuran / 69 h / Ambient temperature

7: 69 percent / N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 41 h / Ambient temperature

8: 1.) O,N-bis(trimethylsilyl)acetamide, 2.) tetrakis(tetraphenylphosphine)palladium⁽⁰⁾, 1,3-bis(diphenylphosphino)propane / tetrahydrofuran / 16 h / Heating; other reagent, solvent, reaction time

9: 1.) OsO₄, 2.) NaHSO₃ / 1.) pyridine, 25 deg C, 5 h, 2.) pyridine-THF-H₂O, 10 min

With 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; 2-methyl-but-2-ene; dimethylsulfide borane complex; tetrakis(tetraphenylphosphine)palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; N,O-bis-(trimethylsilyl)-acetamide; sodium hydrogensulfite; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja00341a043