methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Base Information

Chemical Name:methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate
CAS No.:303191-11-9
Molecular Formula:C₃₅H₄₁NO₄Si
Molecular Weight:567.8
Hs Code.:

Synonyms:methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

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Chemical Property of methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

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Technology Process of methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

There total 26 articles about methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate 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: 84.0%

: 303191-10-8
methyl (2S,3S,4aR,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-4a-hydroxy-2-methyldecahydro-5-quinolinecarboxylate

: 303191-11-9
methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Guidance literature:: With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/jo001589n

Reference yield:

: 164471-44-7
ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-en-ol

: 303191-11-9
methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Guidance literature:: Multi-step reaction with 25 steps

1.1: 85 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

2.1: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

3.1: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / Heating

4.1: 99 percent / DIBAL-H / CH₂Cl₂; hexane / 4 h / 0 °C

5.1: 90 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 3 h / 0 °C

6.1: 91 percent / dimethylsulfoxide / 1 h / 50 °C

7.1: NaOH / H₂O / 4 h / Heating

8.1: 86 percent / diethyl ether / 0.5 h / 0 °C

9.1: 80 percent / hydroxylamine hydrochloride; KOH / methanol / 1 h / 0 °C

10.1: solid tetrapropylammonium (meta)periodate / H₂O; dimethylformamide / 0.5 h / 0 °C

11.1: 99 percent / H₂ / Pd/C / tetrahydrofuran / 0.5 h

12.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

12.2: 1.18 g / (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / 5 h / -78 °C

13.1: imidazole / dimethylformamide / 42 h / 20 °C

14.1: tetrahydrofuran / 0.17 h / 0 °C

14.2: 82 percent / NaBH₃CN; AcOH / tetrahydrofuran / 1 h / 0 °C

15.1: Zn; AcOH / H₂O / 1 h / 60 °C / 7

16.1: 90 percent / KOH; K₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

17.1: NaH; imidazole / tetrahydrofuran / 1 h / Heating

17.2: 98 percent / tetrahydrofuran / 0.5 h / Heating

18.1: 95 percent / tributyltinhydride; 2,2-azobisisobutyronitrile / benzene / 3 h / Heating

19.1: 81 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 3 h / Heating

20.1: 95 percent / H₂ / Pd(OH)2 / methanol / 1.5 h

21.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

22.1: 87 percent / AcOH; piperidine / benzene / 1 h / Heating

23.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

24.1: 75 percent / diethyl ether / 0 °C

25.1: 84 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

With piperidine; 1H-imidazole; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 10.1: intramolecular Diels-Alder reaction / 21.1: Swern oxidation;
DOI:10.1021/jo001589n

Reference yield:

: 164577-87-1
ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-enoate

: 303191-11-9
methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Guidance literature:: Multi-step reaction with 26 steps

1.1: 97 percent / DIBAL-H / tetrahydrofuran; hexane / 0.5 h / 20 °C

2.1: 85 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

3.1: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

4.1: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / Heating

5.1: 99 percent / DIBAL-H / CH₂Cl₂; hexane / 4 h / 0 °C

6.1: 90 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 3 h / 0 °C

7.1: 91 percent / dimethylsulfoxide / 1 h / 50 °C

8.1: NaOH / H₂O / 4 h / Heating

9.1: 86 percent / diethyl ether / 0.5 h / 0 °C

10.1: 80 percent / hydroxylamine hydrochloride; KOH / methanol / 1 h / 0 °C

11.1: solid tetrapropylammonium (meta)periodate / H₂O; dimethylformamide / 0.5 h / 0 °C

12.1: 99 percent / H₂ / Pd/C / tetrahydrofuran / 0.5 h

13.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

13.2: 1.18 g / (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / 5 h / -78 °C

14.1: imidazole / dimethylformamide / 42 h / 20 °C

15.1: tetrahydrofuran / 0.17 h / 0 °C

15.2: 82 percent / NaBH₃CN; AcOH / tetrahydrofuran / 1 h / 0 °C

16.1: Zn; AcOH / H₂O / 1 h / 60 °C / 7

17.1: 90 percent / KOH; K₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

18.1: NaH; imidazole / tetrahydrofuran / 1 h / Heating

18.2: 98 percent / tetrahydrofuran / 0.5 h / Heating

19.1: 95 percent / tributyltinhydride; 2,2-azobisisobutyronitrile / benzene / 3 h / Heating

20.1: 81 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 3 h / Heating

21.1: 95 percent / H₂ / Pd(OH)2 / methanol / 1.5 h

22.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

23.1: 87 percent / AcOH; piperidine / benzene / 1 h / Heating

24.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

25.1: 75 percent / diethyl ether / 0 °C

26.1: 84 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

With piperidine; 1H-imidazole; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 11.1: intramolecular Diels-Alder reaction / 22.1: Swern oxidation;
DOI:10.1021/jo001589n