(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

Base Information

Chemical Name:(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one
CAS No.:366479-75-6
Molecular Formula:C₃₀H₃₅NO₅SSi
Molecular Weight:549.763
Hs Code.:

Synonyms:(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

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Chemical Property of (4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

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Technology Process of (4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

There total 3 articles about (4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one 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: 71.0%

: 1826-67-1
vinyl magnesium bromide

: 366479-74-5
(R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-2,5-dihydro-1H-pyrrol-2-one

: 366479-75-6
(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

Guidance literature:: vinyl magnesium bromide; In tetrahydrofuran; diethyl ether; at -20 ℃; for 0.333333h;

(R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-2,5-dihydro-1H-pyrrol-2-one; With chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/jm010096n

Reference yield:

: 138629-44-4
(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one

: 366479-75-6
(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran / 0.25 h / -25 °C

1.2: 79 percent / tetrahydrofuran / 1 h / -25 °C

2.1: LDA; PhSeBr / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: O₃ / CH₂Cl₂ / -78 °C

2.3: 89 percent / pyridine / CH₂Cl₂ / -78 - 20 °C

3.1: CuCN / diethyl ether; tetrahydrofuran / 0.33 h / -20 °C

3.2: 71 percent / TMSCl / diethyl ether; tetrahydrofuran / 1 h / -78 °C

With Phenylselenyl bromide; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jm010096n

Reference yield:

: 463300-44-9
(R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)pyrrolidin-2-one

: 366479-75-6
(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA; PhSeBr / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: O₃ / CH₂Cl₂ / -78 °C

1.3: 89 percent / pyridine / CH₂Cl₂ / -78 - 20 °C

2.1: CuCN / diethyl ether; tetrahydrofuran / 0.33 h / -20 °C

2.2: 71 percent / TMSCl / diethyl ether; tetrahydrofuran / 1 h / -78 °C

With Phenylselenyl bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jm010096n