(2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

Base Information

Chemical Name:(2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester
CAS No.:196491-88-0
Molecular Formula:C₃₁H₄₇NO₂Si
Molecular Weight:493.805
Hs Code.:

Synonyms:(2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

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Chemical Property of (2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

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Technology Process of (2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

There total 32 articles about (2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl 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:

: 196491-84-6
(S)-3-(Dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester

: 196491-88-0
(2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / BuLi, 2,2,6,6-tetramethylpiperidine, DMPU / tetrahydrofuran; hexane / 1.) -50 deg C, 10 min, 2.) -78 deg C, 12 h; -50 deg C, 48 h

2: 100 percent / KOH, H₂O / methanol; tetrahydrofuran / 32 h / Heating

3: CH₂Cl₂ / 0.5 h / Ambient temperature

4: NH₃ / CH₂Cl₂

5: 75 percent / Pb(OAc)4 / dimethylformamide / 15 h / 100 °C

6: 100 percent / p-TsOH / acetone; H₂O / 2.5 h / Heating

7: H₂ / 10percent Pd/C / ethanol; acetic acid / 7 h / 2740.9 Torr

8: Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

With 2,2,6,6-tetramethyl-piperidine; lead(IV) acetate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; n-butyllithium; ammonia; water; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a808840c

Reference yield:

: 196491-83-5
(S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-tetradecane-1,5-dione

: 196491-88-0
(2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / TMS-OTf / CH₂Cl₂ / 48 h / -20 °C

2: 1.) EtMgBr / 1.) ether, 0 to r.t., 2.) r.t., 15 h

3: 88 percent / BuLi, 2,2,6,6-tetramethylpiperidine, DMPU / tetrahydrofuran; hexane / 1.) -50 deg C, 10 min, 2.) -78 deg C, 12 h; -50 deg C, 48 h

4: 100 percent / KOH, H₂O / methanol; tetrahydrofuran / 32 h / Heating

5: CH₂Cl₂ / 0.5 h / Ambient temperature

6: NH₃ / CH₂Cl₂

7: 75 percent / Pb(OAc)4 / dimethylformamide / 15 h / 100 °C

8: 100 percent / p-TsOH / acetone; H₂O / 2.5 h / Heating

9: H₂ / 10percent Pd/C / ethanol; acetic acid / 7 h / 2740.9 Torr

10: Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

With 2,2,6,6-tetramethyl-piperidine; lead(IV) acetate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; ethylmagnesium bromide; ammonia; water; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a808840c

Reference yield:

: 196491-90-4
(R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid

: 196491-88-0
(2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: Et₃N / tetrahydrofuran / 1 h / 0 °C

2: tetrahydrofuran / 48 h / -25 °C

3: 100 percent / TMS-OTf / CH₂Cl₂ / 48 h / -20 °C

4: 1.) EtMgBr / 1.) ether, 0 to r.t., 2.) r.t., 15 h

5: 88 percent / BuLi, 2,2,6,6-tetramethylpiperidine, DMPU / tetrahydrofuran; hexane / 1.) -50 deg C, 10 min, 2.) -78 deg C, 12 h; -50 deg C, 48 h

6: 100 percent / KOH, H₂O / methanol; tetrahydrofuran / 32 h / Heating

7: CH₂Cl₂ / 0.5 h / Ambient temperature

8: NH₃ / CH₂Cl₂

9: 75 percent / Pb(OAc)4 / dimethylformamide / 15 h / 100 °C

10: 100 percent / p-TsOH / acetone; H₂O / 2.5 h / Heating

11: H₂ / 10percent Pd/C / ethanol; acetic acid / 7 h / 2740.9 Torr

12: Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

With 2,2,6,6-tetramethyl-piperidine; lead(IV) acetate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; ethylmagnesium bromide; ammonia; water; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a808840c