(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:205491-23-2
Molecular Formula:C₃₁H₅₅NO₄Si
Molecular Weight:533.867
Hs Code.:

Synonyms:(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 14 articles about (2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 99.0%

: 100-58-3
phenylmagnesium bromide

: (2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 205491-23-2
(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;
DOI:10.3987/com-97-s19

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 205491-23-2
(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 95 percent / 0.5M aq.Na₂CO₃ / dioxane / Ambient temperature

2: 1.) N-hydroxysuccinimide, DCC; 2.) NaBH₄ / 1.) CH₂Cl₂, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min

3: p-TsOH / CH₂Cl₂ / Ambient temperature

4: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

5: imidazole / CH₂Cl₂ / Ambient temperature

6: 94 percent / PdCl₂(MeCN)2 / acetonitrile / Heating

7: 73 percent / CuBr*SMe₂

8: 91 percent / KH / tetrahydrofuran / Ambient temperature

9: 97 percent / TBAF / tetrahydrofuran / Ambient temperature

11: 1.) O₃; 2.) Me₂S / 1.) MeOH, -78 deg C; 2.) r.t., overnight

12: 99 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; tetrabutyl ammonium fluoride; potassium hydride; sodium carbonate; toluene-4-sulfonic acid; ozone; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; acetonitrile;
DOI:10.3987/com-97-s19

Reference yield:

: 59768-74-0,124184-67-4
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester

: 205491-23-2
(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(hydroxy-phenyl-methyl)-5-nonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) N-hydroxysuccinimide, DCC; 2.) NaBH₄ / 1.) CH₂Cl₂, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min

2: p-TsOH / CH₂Cl₂ / Ambient temperature

3: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

4: imidazole / CH₂Cl₂ / Ambient temperature

5: 94 percent / PdCl₂(MeCN)2 / acetonitrile / Heating

6: 73 percent / CuBr*SMe₂

7: 91 percent / KH / tetrahydrofuran / Ambient temperature

8: 97 percent / TBAF / tetrahydrofuran / Ambient temperature

10: 1.) O₃; 2.) Me₂S / 1.) MeOH, -78 deg C; 2.) r.t., overnight

11: 99 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; tetrabutyl ammonium fluoride; potassium hydride; toluene-4-sulfonic acid; ozone; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.3987/com-97-s19