ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Base Information

Chemical Name:ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate
CAS No.:695176-82-0
Molecular Formula:C₂₂H₃₀O₆
Molecular Weight:390.477
Hs Code.:

Synonyms:ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

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Chemical Property of ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

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Technology Process of ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

There total 19 articles about ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate 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: 86.0%

: 56579-97-6
lithium 1-ethoxyethenolate

: 677729-72-5
4-[(2R,3S,5R,7S)-2,3-epoxy-5,7-isopropylidenedioxy-1-oxo-9-phenylnonyl]morpholine

: 695176-82-0
ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1002/chem.200305709

Reference yield:

: 24271-22-5,55320-96-2,138034-94-3
5-phenyl-2(E)-pentenoic acid

: 695176-82-0
ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: oxalyl chloride / CH₂Cl₂ / 2 h / 20 °C

2.1: 6.53 g / NaHCO₃ / tetrahydrofuran / 0.83 h

3.1: 100 percent / Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (S)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 8 h / 20 °C

4.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / tetrahydrofuran / 6 h / -78 °C

5.1: 79 percent / NaBH₄; PhSeSePh / ethanol / 0.17 h / 0 °C

6.1: BEt₂(OMe) / tetrahydrofuran; methanol / 1 h / -78 °C

6.2: 75 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / -78 °C

7.1: 100 percent / imidazole; DMAP / dimethylformamide / 20 °C

8.1: 97 percent / DIBAL-H / toluene / 3 h / -78 °C

9.1: 94 percent / LiCl; DBU / acetonitrile / 20 °C

10.1: Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (R)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 12 h / 20 °C

11.1: Et₃N*3HF / tetrahydrofuran / 3 h / 20 °C

12.1: 0.14 g / TsOH*H₂O / 20 °C

13.1: 86 percent / tetrahydrofuran / -78 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; oxalyl dichloride; triphenyl-arsane; 4 A molecular sieve; diphenyl diselenide; diethyl methoxy borane; samarium(III) isopropoxide; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); lithium chloride; lithium hexamethyldisilazane; tert.-butylhydroperoxide; (R)-1,1'-Bi-2-naphthol; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; methanol; decane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/chem.200305709

Reference yield:

: 485809-19-6
5-phenyl-2-pentenoic acid chloride

: 695176-82-0
ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 6.53 g / NaHCO₃ / tetrahydrofuran / 0.83 h

2.1: 100 percent / Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (S)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 8 h / 20 °C

3.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 78 percent / tetrahydrofuran / 6 h / -78 °C

4.1: 79 percent / NaBH₄; PhSeSePh / ethanol / 0.17 h / 0 °C

5.1: BEt₂(OMe) / tetrahydrofuran; methanol / 1 h / -78 °C

5.2: 75 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / -78 °C

6.1: 100 percent / imidazole; DMAP / dimethylformamide / 20 °C

7.1: 97 percent / DIBAL-H / toluene / 3 h / -78 °C

8.1: 94 percent / LiCl; DBU / acetonitrile / 20 °C

9.1: Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (R)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 12 h / 20 °C

10.1: Et₃N*3HF / tetrahydrofuran / 3 h / 20 °C

11.1: 0.14 g / TsOH*H₂O / 20 °C

12.1: 86 percent / tetrahydrofuran / -78 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; triphenyl-arsane; 4 A molecular sieve; diphenyl diselenide; diethyl methoxy borane; samarium(III) isopropoxide; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); lithium chloride; lithium hexamethyldisilazane; tert.-butylhydroperoxide; (R)-1,1'-Bi-2-naphthol; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; methanol; decane; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/chem.200305709