1-Piperidinecarboxylic acid, 3-(dimethylphenylsilyl)-6-(8-hydroxyoctyl)-2-methyl-, phenylmethyl ester, (2S,3S,6R)-

Base Information

Chemical Name:1-Piperidinecarboxylic acid, 3-(dimethylphenylsilyl)-6-(8-hydroxyoctyl)-2-methyl-, phenylmethyl ester, (2S,3S,6R)-
CAS No.:477945-89-4
Molecular Formula:C30H45NO3Si
Molecular Weight:495.778
Hs Code.:

Synonyms:

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Chemical Property of 1-Piperidinecarboxylic acid, 3-(dimethylphenylsilyl)-6-(8-hydroxyoctyl)-2-methyl-, phenylmethyl ester, (2S,3S,6R)-

Chemical Property:

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Technology Process of 1-Piperidinecarboxylic acid, 3-(dimethylphenylsilyl)-6-(8-hydroxyoctyl)-2-methyl-, phenylmethyl ester, (2S,3S,6R)-

There total 16 articles about 1-Piperidinecarboxylic acid, 3-(dimethylphenylsilyl)-6-(8-hydroxyoctyl)-2-methyl-, phenylmethyl ester, (2S,3S,6R)- 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: 95.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 477945-88-3
8-[(2R,5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-methyl-piperidin-2-yl]-octan-1-ol

: 477945-89-4
(2S,3S,6R)-3-(Dimethyl-phenyl-silanyl)-6-(8-hydroxy-octyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With potassium carbonate; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(02)01853-1

Reference yield:

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

: 477945-89-4
(2S,3S,6R)-3-(Dimethyl-phenyl-silanyl)-6-(8-hydroxy-octyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: (COCl)2 / dimethylformamide; CH₂Cl₂ / 20 °C

2.1: diethyl ether / 0 °C

3.1: 78 percent / PhCO₂Ag; Et₃N / tetrahydrofuran / 20 °C

4.1: 98 percent / H₂ / Pd-C / ethyl acetate / 20 °C

5.1: Et₃N / tetrahydrofuran / 0 °C

6.1: tetrahydrofuran / -78 °C

7.1: TMSO-Tf / CH₂Cl₂ / -20 °C

8.1: Ti(OEt)4 / Heating

9.1: Li-TMP / tetrahydrofuran / -78 °C

9.2: 74 percent / tetrahydrofuran / -78 - 0 °C

10.1: KOH / methanol; H₂O / Heating

11.1: (Im)2CO / CH₂Cl₂ / 20 °C

11.2: NH₃

12.1: 85 percent / Pb(OAc)4 / dimethylformamide / 100 °C

13.1: 90 percent / TsOH / acetone; H₂O / Heating

14.1: 59 percent / H₂; acetic acid / Pd-C / ethanol / 20 °C / 2068.59 - 2585.74 Torr

15.1: 95 percent / K₂CO₃ / tetrahydrofuran / 20 °C

With lead(IV) acetate; titanium(IV) tetraethanolate; potassium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; silver benzoate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 3.1: Wolff rearrangement / 6.1: Grignard reaction / 12.1: modified Curtius reaction;
DOI:10.1016/S0040-4039(02)01853-1

Reference yield:

: 196491-68-6
3-[dimethyl(phenyl)silyl]glutaric anhydride

: 477945-89-4
(2S,3S,6R)-3-(Dimethyl-phenyl-silanyl)-6-(8-hydroxy-octyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: DMAP / CH₂Cl₂ / 20 °C

2.1: (COCl)2 / dimethylformamide; CH₂Cl₂ / 20 °C

3.1: diethyl ether / 0 °C

4.1: 78 percent / PhCO₂Ag; Et₃N / tetrahydrofuran / 20 °C

5.1: 98 percent / H₂ / Pd-C / ethyl acetate / 20 °C

6.1: Et₃N / tetrahydrofuran / 0 °C

7.1: tetrahydrofuran / -78 °C

8.1: TMSO-Tf / CH₂Cl₂ / -20 °C

9.1: Ti(OEt)4 / Heating

10.1: Li-TMP / tetrahydrofuran / -78 °C

10.2: 74 percent / tetrahydrofuran / -78 - 0 °C

11.1: KOH / methanol; H₂O / Heating

12.1: (Im)2CO / CH₂Cl₂ / 20 °C

12.2: NH₃

13.1: 85 percent / Pb(OAc)4 / dimethylformamide / 100 °C

14.1: 90 percent / TsOH / acetone; H₂O / Heating

15.1: 59 percent / H₂; acetic acid / Pd-C / ethanol / 20 °C / 2068.59 - 2585.74 Torr

16.1: 95 percent / K₂CO₃ / tetrahydrofuran / 20 °C

With lead(IV) acetate; dmap; titanium(IV) tetraethanolate; potassium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; silver benzoate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 4.1: Wolff rearrangement / 7.1: Grignard reaction / 13.1: modified Curtius reaction;
DOI:10.1016/S0040-4039(02)01853-1