Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

Base Information

Chemical Name:Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester
CAS No.:84026-50-6
Molecular Formula:C₂₆H₃₆O₉S
Molecular Weight:524.632
Hs Code.:

Synonyms:Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

There total 11 articles about Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester 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:

: 108-30-5
succinic acid anhydride

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

: 84026-50-6
Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

: 83999-41-1
Succinic acid mono-((3R,6R,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

Guidance literature:: With dmap; In dichloromethane; at 25 ℃; for 23h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/ja00341a043

Reference yield:

: 112-45-8
10-Undecenal

: 84026-50-6
Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

Guidance literature:: Multi-step reaction with 11 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

11: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 23 h / 25 °C

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

: 84026-50-6
Succinic acid mono-((3R,6S,16R)-3-benzenesulfonyl-16-methyl-2,5-dioxo-oxacyclohexadec-6-yl) ester

Guidance literature:: Multi-step reaction with 10 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

10: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 23 h / 25 °C

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